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Xantphos

Xantphos is a versatile phosphine ligand used in various catalytic reactions, including cross-coupling, hydrogenation, and carbonylation.
This bidentate ligand offers unique steric and electronic properties that can enhance the activity and selectivity of transition metal catalysts.
Researchers can optimize their Xantphos-based protocols using PubCompare.ai's AI-driven platform, which helps identify the most effective literature, preprint, and patent-derived methods.
Leveraging advanced search and comparison tools, scientists can streamline their research process and obtain better results with Xantphos.
PubCompare.ai's AI-powered insights can also assist in selecting the most appropriate Xantphos products for their specific applications.

Most cited protocols related to «Xantphos»

Carbonylative Amidation of Aryl Halides

Cited 2 times

An oven-dried culture tube (18 × 150 mm) equipped with a Teflon® coated magnetic stir bar was sealed with a 14/20 rubber septum (inverted), evacuated, backfilled with nitrogen and cooled under nitrogen. Pd(OAc)2 (2 mol %, 0.02 mmol, 0.02 equiv., 4.5 mg), Xantphos (2 mol %, 0.02 mmol, 0.02 equiv., 11.6 mg), N, O-dimethylhydroxylamine hydrochloride (1.5 mmol, 1.5 equiv., 146 mg), and Na₂CO₃ (3 mmol, 3 equiv., 318 mg) were added by briefly removing the rubber septum. The rubber septum then was secured with several wrappings of electrical tape. 4-bromo-2-fluorobenzonitrile (1 mmol, 0.200 g) and toluene (2 mL) were added dropwise via syringe. The reaction then was purged for ~ 30 seconds with CO_(g); following the gas purge a balloon was connected to the reaction using a short length of rubber tubing (~ 1 in.), a needle adapter and a 20 G needle. This balloon was then inflated with CO_(g), and the reaction tube was submerged in a 80 °C preheated oil bath. The reaction mixture was heated at 80 °C with vigorous stirring until the aryl halide had been completely consumed as judged by GC analysis (18 h). The reaction mixture was then allowed to cool to room temperature, diluted with ethyl acetate (~ 10 mL), filtered through a plug of celite (eluting with ethyl acetate) and concentrated under reduced pressure. The crude product mixture was purified by flash column chromatography on silica gel (20 % –50 % ethyl acetate in hexanes) to provide the title compound as a light yellow-orange solid (181 mg, 95 %), mp 43 – 44 °C. ¹H NMR (300 MHz, CDCl₃) δ: 7.71-7.66 (m, 1H), 7.60-7.52 (m, 2H), 3.54 (s, 3H), 3.38 (s, 3H). ¹³C NMR (75 MHz, CDCl₃) δ: 166.38, 164.23, 160.79, 140.84, 140.74, 133.36, 124.70, 124.65, 116.64, 116.35, 113.42, 103.26, 103.06, 61.59, 33.17 (observed complexity due to C-F splitting; definitive assignments have not yet been made). ¹⁹F NMR (282 MHz, CDCl₃) δ: −106.1. IR (neat, cm⁻¹): 3090, 2977, 2940, 2823, 2239, 1652, 1622, 1566, 1503, 1459, 1428, 1386, 1251, 1198, 1182, 1115, 990, 941, 887, 835, 750, 733, 714, 682, 668. Anal. Calcd for C₁₀H₉FN₂O₂: C, 57.69; H, 4.36. Found: C, 57.64; H, 4.37.

Martinelli J.R., Watson D.A., Freckmann D.M., Barder T.E, & Buchwald S.L. (2008). Palladium-Catalyzed Carbonylation Reactions of Aryl Bromides at Atmospheric Pressure: A General System Based on Xantphos. The Journal of organic chemistry, 73(18), 7102-7107.

Publication 2008

1H NMR Anus Bath Carbon-13 Magnetic Resonance Spectroscopy Celite Chromatography Electricity ethyl acetate Hexanes Light Needles Neoplasm Metastasis Nitrogen Pressure Rubber Silica Gel Syringes Teflon Toluene xantphos

Synthesis of 1-Cyclobutyl-4-(3-isothiocyanatophenyl)piperazine

Cited 2 times

The syntheses of final compounds 10–12, 20–23, 34–37 and 43 are described in the Supplementary Materials.
Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate (39). A solution of bromide 38 (808 mg, 4.00 mmol) and NaOtBu (461 mg, 4.80 mmol) in dioxane (15 mL) was degassed with N₂ for 10 min. Next, Pd₂(dba)₃ (183 mg, 0.20 mmol), Xantphos (347 mg, 0.60 mmol) and tert-butyl piperazine-1-carboxylate (1.12 g, 6.00 mmol) were added. The reaction mixture was heated for 1 h at 80 °C under microwave irradiation. The reaction mixture was diluted with water (40 mL) and extracted with DCM (3 × 30 mL). The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. Purification by flash chromatography (heptane:EtOAc 5:0 to 4:1) gave the title compound as an orange solid (700 mg, 57%). ¹H NMR (500 MHz, CDCl₃) δ 7.72 (t, J. = 2.2 Hz, 1H), 7.71–7.67 (m, 1H), 7.39 (t, J. = 8.2 Hz, 1H), 7.20 (dd, J. = 8.3, 2.1 Hz, 1H), 3.61 (t, J. = 5.2 Hz, 4H), 3.24 (t, J. = 5.1 Hz, 4H), 1.49 (s, 9H). HPLC-MS (acidic mode): t_R = 5.3 min, purity: 98.6%, [M + H]⁺: 308.
1-(3-Nitrophenyl)piperazine (40). To a solution of carbamate 39 (1.20 g, 3.90 mmol) in dioxane (20 mL) was added HCl in dioxane (4N, 9.75 mL, 39.0 mmol). The reaction mixture was stirred for 1 h at rt. The solvent was removed under reduced pressure. The residue was mixed with satd. aq. Na₂CO₃ (40 mL) and extracted with DCM (3 × 30 mL). The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. The title compound was obtained as a brown solid (633 mg, 78%). ¹H NMR (500 MHz, CDCl₃) δ 7.71 (s, 1H), 7.66 (d, J. = 8.0 Hz, 1H), 7.37 (t, J. = 8.2 Hz, 1H), 7.19 (d, J. = 8.3 Hz, 1H), 3.28–3.21 (m, 4H), 3.10–3.02 (m, 4H). HPLC-MS (acidic mode): t_R = 2.6 min, purity: 97.3%, [M + H]⁺: 208.
1-Cyclobutyl-4-(3-nitrophenyl)piperazine (41). To a solution of amine 40 (630 mg, 3.04 mmol) in DCM (20 mL) was added cyclobutanone (273 μL, 3.66 mmol). After 10 min of stirring at rt, NaBH(OAc)₃ (966 mg, 4.56 mmol) was added and the resulting mixture was stirred at rt overnight. The reaction mixture was quenched with satd. aq. Na₂CO₃ (30 mL) and extracted with DCM (3 × 15 mL). The combined organic phases were dried over Na₂SO₄, filtered and concentrated in vacuo. Purification by flash chromatography (DCM:MeOH 20:0 to 19:1) gave the title compound as a yellow oil (600 mg, 76%). ¹H NMR (500 MHz, CDCl₃) δ 7.71 (t, J. = 2.3 Hz, 1H), 7.65 (dd, J. = 8.1, 1.5 Hz, 1H), 7.37 (t, J. = 8.2 Hz, 1H), 7.18 (dd, J. = 8.3, 2.1 Hz, 1H), 3.38–3.23 (m, 4H), 2.80 (p, J. = 7.9 Hz, 1H), 2.51 (t, J. = 5.1 Hz, 4H), 2.13–2.04 (m, 2H), 2.00–1.87 (m, 2H), 1.81–1.57 (m, 2H, overlaps with residual water). HPLC-MS (acidic mode): t_R = 2.8 min, purity: 97.8%, [M + H]⁺: 262.
3-(4-Cyclobutylpiperazin-1-yl)aniline (42). To a solution of nitrocompound 41 (59 mg, 0.23 mmol) in MeOH (2 mL) was added HCOONH₄ (71 mg, 1.13 mmol) as a solid followed by a suspension of Pd/C (10%, 24 mg) in water (2 mL). The reaction mixture was stirred at rt overnight. The mixture was filtered over Celite and the filtrate was concentrated in vacuo. The residue was diluted with aq. Na₂CO₃ (1.0 M, 10 mL) and extracted with DCM (3 × 5 mL). The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (DCM:MeOH 20:0 to 19:1). The selected fractions were collected and the solvents were evaporated. The residue was dissolved in aq. HCl (1.0 M, 10 mL), washed with EtOAc (2 × 5 mL) and c-hexane (3 × 10 mL). The pH of the aqueous layer was adjusted to 10 with satd. aq. Na₂CO₃ and extracted with EtOAc (3 × 10 mL). The combined organic phases were dried over Na₂SO₄, filtered and concentrated in vacuo. The title compound was obtained as an off-white solid (13 mg, 25%). Mp: 92.5–92.7 °C. ¹H NMR (500 MHz, CDCl₃) δ 7.04 (t, J. = 8.0 Hz, 1H), 6.36 (dd, J. = 8.2, 2.3 Hz, 1H), 6.25 (t, J. = 2.3 Hz, 1H), 6.21 (dd, J. = 7.7, 2.0 Hz, 1H), 3.59 (br, 2H), 3.26–3.10 (m, 4H), 2.78 (p, J. = 7.9 Hz, 1H), 2.56–2.37 (m, 4H), 2.12–2.02 (m, 2H), 2.00–1.88 (m, 2H), 1.80–1.64 (m, 2H). ¹³C NMR (126 MHz, CDCl₃) δ 152.6, 147.4, 130.0, 107.1, 107.1, 103.0, 60.4, 49.6, 48.8, 27.1, 14.4. HPLC-MS (basic mode): t_R = 4.1 min, purity: 98.4%, [M + H]⁺: 232. HR-MS [M + H]⁺ calcd for C₁₄H₂₂N₃⁺: 232.1808, found 232.1818.
1-Cyclobutyl-4-(3-isothiocyanatophenyl)piperazine (44). To an ice-cold mixture of aniline 42 (46 mg, 0.20 mmol) in DCM (2 mL) and aq. NaHCO₃ (1.0 M, 30 mL) was added dropwise a solution of CSCl₂ (18 μL, 0.24 mmol) in DCM (1 mL). The reaction mixture was stirred for 1 h at rt. The reaction mixture was diluted with water (10 mL) and extracted with DCM (3 × 5 mL). The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. Purification by flash chromatography (DCM:MeOH 20:0 to 19:1) gave the title compound as a white solid (35 mg, 64%). The compound is stable as a solid in the freezer (−20 °C) over a period of at least 2 years as judged by NMR and LC-MS analysis. Mp: 79.7–80.1°C. ¹H NMR (500 MHz, CDCl₃) δ 7.18 (t, J. = 8.1 Hz, 1H), 6.81 (dd, J. = 8.5, 2.4 Hz, 1H), 6.72–6.65 (m, 2H), 3.23–3.15 (m, 4H), 2.77 (p, J. = 7.9 Hz, 1H), 2.50–2.42 (m, 4H), 2.11–2.02 (m, 2H), 1.96–1.86 (m, 2H), 1.79–1.64 (m, 2H). ¹³C NMR (126 MHz, CDCl₃) δ 152.2, 134.2, 131.9, 130.0, 116.5, 114.9, 112.6, 60.3, 49.3, 48.3, 27.1, 14.4. HPLC-MS (acidic mode): t_R = 3.6 min, purity: 98.9%, [M + H]⁺: 274. HR-MS [M + H]⁺ calcd for C₁₅H₂₀N₃S⁺: 274.1372, found 274.1374.

Wágner G., Mocking T.A., Kooistra A.J., Slynko I., Ábrányi-Balogh P., Keserű G.M., Wijtmans M., Vischer H.F., de Esch I.J, & Leurs R. (2019). Covalent Inhibition of the Histamine H3 Receptor. Molecules, 24(24), 4541.

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Publication 2019

Synthesis of Amidine Compound 39

Cited 1 time

To a flame-dried vial filled with nitrogen was added Pd₂(dba)₃ (8.90 mg, 0.010 mmol), xantphos (11.2 mg, 0.020 mmol), and anhyd THF (4 mL). The resulting solution was stirred at rt for 10 min. Subsequently, a respective ynamide (79.0 mg, 0.20 mmol), K₂CO₃ (27.8 mg, 0.20 mmol), and pyrollidine (49.0 μL, 0.60 mmol) were added. The reaction mixture was stirred under nitrogen at 65 °C for 6 h. The progress of the reaction was monitored by TLC. After complete consumption of the starting ynamide, the crude reaction mixture was filtered through Celite^™ and concentrated in vacuo. Purification of the crude residue via silica gel flash column chromatography [isocratic eluent: 5:1 hexanes/EtOAc] afforded amidine 39 (95.0 mg, 0.20 mmol, ≥95%).
39: Rf = 0.22 [5:1 hexanes:EtOAc]; white solid; mp 75 – 76 °C; ¹H NMR (400 MHz, CDCl3) delta; 0.98 (d, 18H, J = 6.0 Hz), 1.16 (m, 3H), 1.76 – 1.82 (m, 1H), 1.92 – 2.08 (m, 3H), 2.17 – 2.22 (m, 1H), 2.26 – 2.29 (m, 1H), 2.38 (s, 3H), 2.44 – 2.52 (m, 1H), 3.56 (q, 1H, J = 8.0 Hz), 3.68 (td, 1H, J = 2.4, 8.0 Hz), 4.22 (brs, 2H), 4.97 (d, 1H, J = 10.8 Hz), 5.02 (d, 1H, J = 17.6 Hz), 5.81 (m, 1H), 7.20 (d, 2H, J = 8.4 Hz), 7.78 (d, 2H, J = 8.4 Hz); ¹³C NMR (125 MHz, CDCl3) δ 11.5, 19.1, 21.5, 25.4, 25.8, 35.8, 35.9, 51.8, 53.2, 116.0, 126.1, 128.8, 137.8, 140.9, 143.2, 167.1; IR (neat) cm⁻¹ 2924ms, 2863m, 1547s, 1414s, 1274s, 1139s; mass spectrum (APCI): m/e (% relative intensity) 463 (100) (M+H)⁺. HRMS (ESI) m/e calcd for C₂₅H₄₂N₂O₂SSiNa 485.2628, found 486.2630.

DeKorver K.A., Johnson W.L., Zhang Y., Hsung R.P., Dai H., Deng J., Lohse A.G, & Zhang Y.S. (2011). N-Allyl-N-Sulfonyl Ynamides as Synthetic Precursors to Amidines and Vinylogous Amidines. An Unexpected N-to-C 1,3-Sulfonyl Shift in Nitrile Synthesis. The Journal of organic chemistry, 76(12), 5092-5103.

Publication 2011

1H NMR Amidines Carbon-13 Magnetic Resonance Spectroscopy Celite Chromatography Gel Chromatography Hexanes Mass Spectrometry Nitrogen potassium carbonate Silica Gel Silicon Dioxide xantphos

MCD Spectroscopy of Frozen Solutions

Cited 1 time

All samples for MCD spectroscopy
were prepared in an inert atmosphere glovebox equipped with a liquid
nitrogen fill port to allow sample freezing to 77 K within the glovebox.
Frozen solution MCD samples were prepared in a 6:1 (v:v) toluene-d₈/benzene-d₆ mixture
(mixtures used to afford low-temperature optical glasses) in copper
cells fitted with quartz disks and a 3 mm gasket. For FeCl₂(Xantphos), solid state mulls were prepared using ground polycrystalline
sample and paratone oil as a mulling agent. NIR MCD experiments were
conducted using a Jasco J-730 spectropolarimeter and a liquid nitrogen-cooled
InSb detector. The spectral range accessible with this NIR MCD setup
is 2000–600 nm. UV–visible (UV–vis) MCD spectra
were collected using a Jasco J-715 spectropolarimeter and a shielded
S-20 photomultiplier tube. Both instruments utilize a modified sample
compartment incorporating focusing optics and an Oxford Instruments
SM4000-7T superconducting magnet/cryostat, permitting measurements
from 1.6 to 290 K with magnetic fields of up to 7 T. A calibrated
Cernox sensor directly inserted into the copper sample holder is used
to measure the temperature at the sample to ±0.001 K. All MCD
spectra were baseline-corrected against zero-field scans. VTVH-MCD
spectra were analyzed using previously reported fitting procedures.^{50 (link),51 (link)} For VTVH-MCD fitting, both negative and positive zero-field splitting
models were evaluated. The reported error bars were determined via
evaluation of the effects of systematic variations of the fit parameters
on the quality of the overall fit.

Kneebone J.L., Fleischauer V.E., Daifuku S.L., Shaps A.A., Bailey J.M., Iannuzzi T.E, & Neidig M.L. (2015). Electronic Structure and Bonding in Iron(II) and Iron(I) Complexes Bearing Bisphosphine Ligands of Relevance to Iron-Catalyzed C–C Cross-Coupling. Inorganic Chemistry, 55(1), 272-282.

Publication 2015

Atmosphere Benzene Copper Eye Eyeglasses Freezing Low Vision Magnetic Fields Nitrogen Quartz Radionuclide Imaging Toluene xantphos

Synthesis of Triazolopyridine Carboxylic Acid

Cited 1 time

Step A: A mixture of 50 (0.080 g, 0.167 mmol), Mo(CO)₆ (0.066 g, 0.251 mmol), Pd(OAc)₂ (0.0037 g, 0.0167 mmol), xantphos (0.014 g, 0.0251 mmol), CH₃OH (0.054 g, 1.67 mmol), Cs₂CO₃ (109 g, 0.334 mmol), and 1,4-dioxane (2 mL) was heated at 80 °C for 2 h in a sealed vessel. The mixture was allowed to cool to rt and then directly chromatographed over silica gel (0–60% EtOAc in hexanes) to give methyl 3-((3aR,5R,6aS)-5-(2-(trifluoromethyl)phenyl)octahydrocyclopenta[c]pyrrole-2-carbonyl)-3.88triazolo[4,3-a]pyridine-6-carboxylate as a white solid (0.024 g, 31%): ¹H NMR (300 MHz, CDCl₃) δ 10.21 (s, 1H), 8.00–7.87 (m, 2H), 7.63–7.47 (m, 3H), 7.28 (m³, 1H), 4.52–4.21 (m, 2H), 4.03–3.88 (m, 5H), 3.65–3.53 (m, 1H), 3.06–2.89 (m, 2H), 2.47–2.36 (m, 2H), 1.73–1.61 (m, 2H); MS (ESI+) m/z 459 [M + H]⁺.
Step B: To a solution of 3-((3aR,5R,6aS)-5-(2-(trifluoromethyl)-phenyl)octahydrocyclopenta[c]pyrrole-2-carbonyl)-[1,2,4]triazolo-[4,3-a]pyridine-6-carboxylate (0.024 g, 0.0523 mmol) in THF (2 mL) was added a solution of LiOH₂O (0.004 g, 0.105 mmol) in H₂O (1 mL). The mixture was stirred for 30 min at rt, acidified to pH 6 with 2 N aqueous HCl, and subsequently purified by C18 reverse phase column chromatography (10–60% CH₃CN in H₂O) to give 3-((3aR,5R,6aS)-5-(2-(trifluoromethyl)phenyl)octahydrocyclopenta[c]-pyrrole-2-carbonyl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid (5.1) as a white solid (0.020 g, 86%): ¹H NMR (300 MHz, DMSO-d₆) δ 9.51 (s, 1H), 7.98 (d, J = 9.3 Hz, 1H), 7.80–7.74 (m, 2H), 7.6(5–7.61 (m, 2H), 7.38 (t, J = 7.5 Hz, 1H), 4.29–4.18 (m, 2h), 3.88–3.78 (m, 2H), 3.41 (m, 1H), 2.97–2.82 (m, 2H), 2.32–2.19 (m, 2H), 1.71 −1.66 (m, 2H); MS (ESI+) m/z 445 [M + H]⁺; HPLC 97.8% purity (AUC), t_R = 12.8 min (method A).

Cioffi C.L., Racz B., Varadi A., Freeman E.E., Conlon M.P., Chen P., Zhu L., Kitchen D.B., Barnes K.D., Martin W.H., Pearson P.G., Johnson G., Blaner W.S, & Petrukhin K. (2019). Design, Synthesis, and Preclinical Efficacy of Novel Nonretinoid Antagonists of Retinol-Binding Protein 4 in the Mouse Model of Hepatic Steatosis. Journal of medicinal chemistry, 62(11), 5470-5500.

Publication 2019

1H NMR Blood Vessel Carboxylic Acids Chromatography, Reverse-Phase dioxane Hexanes High-Performance Liquid Chromatographies pyridine Pyrrole Silica Gel Sulfoxide, Dimethyl xantphos

Most recents protocols related to «Xantphos»

Synthesis of 4-aminosulfonyl-substituted piperidine compound

Not available on PMC !

Example 1

[Figure (not displayed)]

Example 2

[Figure (not displayed)]

This compound was prepared in an analogous fashion to Example 1, Step 6 using 1-(methylsulfonyl)piperidin-4-amine in place of 4-aminobenzenesulfonamide and RuPhos Pd G2 in place of XantPhos Pd G2. LCMS calculated for C₂₀H₃₂N₅O₃S (M+H)⁺: m/z=422.2; Found: 422.2. ¹H NMR (600 MHz, DMSO) δ 8.01 (s, 1H), 5.44-5.22 (m, 1H), 3.85 (bs, 1H), 3.59 (d, J=12.3 Hz, 1H), 2.9 (s, 3H), 2.85 (t, J=12.2, 2.6 Hz, 1H), 2.60 (s, 2H), 2.05 (s, 1H), 1.98 (d, J=16.3 Hz, 1H), 1.93-1.87 (m, 1H), 1.74 (s, 1H), 1.59 (m, 2H), 1.09 (s, 6H).

US11866432B2. Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors (2024-01-09). Incyte Corporation [US]. Inventors: Alexander Sokolsky [US], Liangxing Wu [US], Wenqing Yao [US].

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Patent 2024

1H NMR Amines CDK2 protein, human inhibitors Laser Capture Microdissection Pyrimidinones Sulfoxide, Dimethyl xantphos

Palladium-Catalyzed Cross-Coupling Reaction

An oven-dried sealed tube containing a stirring bar was charged with Pd(OAc)₂ (5.6 mg, 0.025 mmol, 5 mol%) and XantPhos (14.5 mg, 0.025 mmol, 5 mol%). The sealed tube was then evacuated and backfilled with nitrogen gas three times. The anhydrous DMF (2 mL), aryl fluorosulfate 1 (0.5 mmol, 1 equiv.), aryl formate 2 (1.0 mmol, 2 equiv.), and Et₃N (101.2 mg, 1.0 mmol, 2 equiv.) were then added under nitrogen atmosphere. The reaction mixture was stirred at 80 °C (oil bath) for 12 h before quenching with saturated NH₄Cl solution (10 mL) and extracting with EtOAc (20 mL × 3). The organic layers were combined, washed with saturated brine, and dried over Na₂SO₄. The extracts were concentrated under reduced pressure to obtain the crude product, which was further purified through silica gel column chromatography (using EtOAc/petroleum ether as eluents) to yield the products 3-4.

Chen X., Liang Y., Wang W.W., Miao C., Chu X.Q., Rao W., Xu H., Zhou X, & Shen Z.L. (2024). Palladium-Catalyzed Esterification of Aryl Fluorosulfates with Aryl Formates. Molecules, 29(9), 1991.

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Publication 2024

Borylation of Skipped Dienes

CuCl (0.98 mg, 10 mol%, 0.01 mmol), bis(pinacolato)diboron (60.9 mg, 1.2 equiv, 0.24 mmol), and Xantphos (138.8 mg, 10 mol%, 0.01 mmol) were placed in an oven‐dried reaction vial. The vial was sealed with a screw cap containing a Teflon‐coated rubber septum. The vial was connected to a vacuum/nitrogen manifold through a needle, evacuated, and backfilled with nitrogen and THF (0.24 mL, 1 M). KO^tBu (26.9 mg, 1.2 equiv, 0.24 mmol) in THF (0.24 mL, 1 M) was added to the vial through the rubber septum. Then, the borylated (E) skipped dienes (1 equiv, 0.2 mmol) in THF (0.2 mL, 1 M) were added dropwise at 30 °C for 16 h. After the reaction was complete, 1 mL MeOH was added and stirred for 10 min and the reaction mixture was filtered over Celite. The organic extracts were then concentrated under vacuum and the NMR yield was calculated through comparison to an internal standard (naphthalene). The crude residue was purified by silica gel flash chromatography to obtain the desired product.

Dominguez‐Molano P., Solé‐Daura A., Carbó J.J, & Fernández E. (2024). Remote 1,4‐Carbon‐to‐Carbon Boryl Migration: From a Mechanistic Challenge to a Valuable Synthetic Application of Bicycles. Advanced Science, 11(16), 2309779.

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Publication 2024

Palladium-Catalyzed Benzenesulfination of Aryl Iodide

To the solution of methyl 2-(benzyloxy)-5-iodobenzoate (I12) (200 mg, 0.54 mmol) and benzenesulfinic acid sodium salt (107 mg, 0.65 mmol) in toluene (3.0 mL) under argon were added Pd₂(dba)₃ (15 mg, 0.016 mmol), Xantphos (19 mg, 0.033 mmol), Cs₂CO₃ (265 mg, 0.82 mmol), and nBu₄NCl (181 mg, 0.65 mmol). The mixture was heated at 80°C for 1 h. After cooling, the reaction mixture was diluted with EtOAc, washed with water, dried over Na₂SO₄, and concentrated under reduced pressure. The reaction mixture was purified by chromatography (silica gel, 80/20 v/v n-hexane/ EtOAc) to give product (130 mg, 63% yield). ¹H NMR (400 MHz, CDCl₃) δ 8.39 (d, J = 2.5 Hz, 1H), 7.99 (dd, J = 8.9, 2.5 Hz, 1H), 7.96–7.89 (m, 2H), 7.60–7.53 (m, 1H), 7.53–7.47 (m, 2H), 7.47–7.41 (m, 2H), 7.38 (t, J = 7.2 Hz, 2H), 7.36–7.28 (m, 1H), 7.08 (d, J = 8.9 Hz, 1H), 5.23 (s, 2H), 3.91 (s, 3H). LC-MS: m/z calculated for C₂₁H₁₉O₅S [M+ H⁺]: 383; found 383.

Bobrovs R., Bolsakova J., Buitrago J.A., Varaceva L., Skvorcova M., Kanepe I., Rudnickiha A., Parisini E, & Jirgensons A. (2024). Structure-based identification of salicylic acid derivatives as malarial threonyl tRNA-synthetase inhibitors. PLOS ONE, 19(4), e0296995.

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Publication 2024

Suzuki-Miyaura Coupling of 35a to Prepare 22

Under inert atmosphere, to a solution of 35a (50 mg, 0.11 mmol, 1 equiv) in dioxane(1.5 mL) was added
1-methylimidazol-4-amine (16 mg, 0.166 mmol, 1.5 equiv), Xantphos
(19 mg, 0.033 mmol, 0.3 equiv), Pd₂(dba)₃ (10
mg, 0.011 mmol, 0.1 equiv), and Cs₂CO₃ (108
mg, 0.33 mmol, 3 equiv). The mixture was stirred at 90 °C for
3 h in a sealed vial, then quenched with water, extracted with AcOEt
(twice). The combined layers were passed on a phase separator and
concentrated under reduced pressure. The residue was purified by preparative
HPLC to give 22 as formic acid salt (18 mg, 35%). ¹H NMR (400 MHz, DMSO-d₆) δ
ppm 8.81 (s, 1H), 8.40 (d, J = 7.5 Hz, 1H), 8.33
(d, J = 4.5 Hz, 1H), 8.14 (s, 1H), 7.60 (s, 1H),
7.46 (d, J = 1.4 Hz, 1H), 7.22 (t, J = 74.0 Hz, 1H), 7.11 (d, J = 1.3 Hz, 1H), 7.06
(d, J = 2.3 Hz, 1H), 6.96 (dd, J = 5.0, 1.3 Hz, 2H), 6.83 (dd, J = 7.6, 2.4 Hz,
1H), 3.87 (s, 3H), 3.66 (s, 3H), 2.81–2.75 (m, 1H), 0.72–0.64
(m, 2H), 0.50–0.43 (m, 2H). LC-MS: m/z = 469.3 [M+H].

Peixoto C., Joncour A., Temal-Laib T., Tirera A., Dos Santos A., Jary H., Bucher D., Laenen W., Pereira Fernandes A., Lavazais S., Delachaume C., Merciris D., Saccomani C., Drennan M., López-Ramos M., Wakselman E., Dupont S., Borgonovi M., Roca Magadan C., Monjardet A., Brys R., De Vos S., Andrews M., Jimenez J.M., Amantini D, & Desroy N. (2024). Discovery of Clinical Candidate GLPG3970: A Potent and Selective Dual SIK2/SIK3 Inhibitor for the Treatment of Autoimmune and Inflammatory Diseases. Journal of Medicinal Chemistry, 67(7), 5233-5258.

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What is Xantphos and how is it used in catalytic reactions?

Xantphos is a versatile phosphine ligand that is widely used in various catalytic reactions, including cross-coupling, hydrogenation, and carbonylation. This bidentate ligand offers unique steric and electronic properties that can enhance the activity and selectivity of transition metal catalysts. Researchers often use Xantphos-based protocols to optimize their catalytic processes and achieve better results.

What are some common challenges in using Xantphos for catalytic applications?

One of the main challenges in using Xantphos is finding the most effective protocol for a specific application. Researchers may need to sift through a large volume of literature, preprints, and patents to identify the optimal Xantphos-based method for their needs. Additionally, understanding the nuances of different Xantphos variations and how they impact catalytic performance can be a time-consuming process.

How can PubCompare.ai help researchers optimize their use of Xantphos?

PubCompare.ai's AI-driven platform can greatly assist researchers in optimizing their Xantphos-based protocols. The platform allows you to efficiently screen a vast database of literature, preprints, and patents to identify the most effective Xantphos protocols for your specific research goals. Teh platform's AI-powered analysis can also highlight key differences in protocol effectiveness, enabling you to choose the best option for reproducibility and accuracy. By leveraging PubCompare.ai's advanced search and comparison tools, you can streamline your research process and obtain better results with Xantphos.

What are some of the different variations or types of Xantphos available?

Xantphos comes in several different variations, each with its own unique properties and applications. For example, there are electron-rich and electron-deficient versions of Xantphos that can be used to fine-tune the electronic environment around the catalyst. Additionally, some Xantphos derivatives incorporate substituents that alter the steric bulk or solubility of the ligand. Researchers can use PubCompare.ai to explore the nuances of different Xantphos types and identify the most suitable option for their specific catalytic needs.

What are some of the key applications of Xantphos in catalysis?

Xantphos is a versatile ligand that has been employed in a wide range of catalytic applications. It is commonly used in cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, where it can enhance reactivity and selectivity. Xantphos is also widely used in hydrogenation and carbonylation reactions, where its unique steric and electronic properties can lead to improved catalyst performance. By leveraging PubCompare.ai's AI-powered insights, researchers can quickly identify the most effective Xantphos-based protocols for their specific catalytic applications.

More about "Xantphos"

Xantphos is a versatile bidentate phosphine ligand that has been widely used in a variety of catalytic reactions, such as cross-coupling, hydrogenation, and carbonylation.
This ligand offers unique steric and electronic properties that can enhance the activity and selectivity of transition metal catalysts.
Researchers can optimize their Xantphos-based protocols using PubCompare.ai's AI-driven platform, which helps identify the most effective literature, preprint, and patent-derived methods.
Leveraging advanced search and comparison tools, scientists can streamline their research process and obtain better results with Xantphos.
PubCompare.ai's AI-powered insights can also assist in selecting the most appropriate Xantphos products for their specific applications.
This includes exploring related compounds and techniques, such as Initiator microwave, HP-Sil column, Isolera SNAP 10 g, SCX-2, APEX2, Isolera SNAP, Silica gel 60, CombiFlash Rf unit, and Pd(OAc)2.
By utilizing PubCompare.ai's platform, researchers can easily locate the best Xantphos protocols from a wide range of sources, including literature, pre-prints, and patents.
The AI-powered insights provided by the platform can help scientists identify the most effective Xantphos-based methods and products, streamlining their research process and leading to better results.
With the help of PubCompare.ai, researchers can optimize their Xantphos-related workflows and make more informed decisions about their experimental design and product selection.