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4 protocols using 3 bromopyridine

1

Synthesis of N-Substituted Pyridines

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Silver(i) nitrate was purchased from Lachema (Czech Republic), dimethyl sulfoxide (DMSO), palladium(ii) acetate (Pd(OAc)2) and 3-bromopyridine from Sigma-Aldrich Chemie, 2-bromopyridine, diisopropyl phosphite and N,N-diisopropylethylamine from Fluka, 1,1′-bis(diphenylphosphino)ferrocene (dppf) from Alfa Aesar, bromotrimethylsilane from Acros, dichloromethane, methanol and acetonitrile from VWR Chemicals.
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2

Synthesis of Functionalized Norbornene Derivatives

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Example 1

Materials: The following materials were purchased and used as received.

Dimethyl 5-norbornene-2,3-dicarboxylate (C3) was purchased from Alfa Aesar,

Dichloromethane (DCM) was stored over activated Alumina and purged with Argon before use, Isopropyl alcohol (IPA), dicyclopentadiene (DCPD), 1H,1H,2H-Perflouro-1-octene (PF6), 1H,1H,2H-Perflouro-1-dodecene (PF10), toluene, thionyl chloride, ethylacetate, dimethylformamide (DMF), Maleimide, furan, diisopropylazodicarboxylate (DIAD), triphenylphosphine (Ph3P), 1-haxadecanol, tetrahydrofuran (THF), ethyl acetate, N-phenylMaleimide, acetonitrile, methanol, Grubbs second generation catalyst, 3-bromopyridine, and pentane were obtained from Sigma-Aldrich Co. and used without further treatment. Dichloropentane, also obtained from Sigma-Aldrich Co., was treated with basic alumina before use. Cyclooctadiene (COD) was purified by vacuum distillation from boron trifluoride and used fresh.

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3

Synthesis of Ruthenium Catalysts and Ionic Liquids

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Chromium-coated tungsten
rods were purchased from R.D. Mathis, gold shot (99.99%) was acquired
from J&J Materials, and silicon (100) wafers were obtained from
WRS Materials. A Millipore Elix filtration system was used to produce
deionized water (≥10.0 MΩ).
The following chemicals
were purchased from Sigma-Aldrich and used without further modification:
3-bromopyridine, 4-mercapto-1-butanol (95%), dicyclopentadiene (98%),
Grubbs catalyst second generation [(H2IMes)(PCy3)(Cl)2Ru = CHph], and trans-3,6-endomethylene-1,2,3,6-tetrahydrophthaloyl
chloride (NBDAC). The following chemicals were purchased from Fisher
Scientific and used without further modification: allyl bromide (99%),
1,2-dichloroethane (DCE), 1,2-dimethylimidazole (98%, dMIm), ethanol
(200 Proof), methylene chloride (DCM), potassium bis(fluorosulfonyl)imide
(KFSI), potassium hexafluorophosphate (KPF6), and potassium
perchlorate (KClO4).
Grubbs third generation catalyst
([(H2IMes) (3-Br-py)2(Cl)2Ru = CHPh])
was synthesized as described by
Love et al.30 (link) 3-[(bicyclo[2.2.1]hept-5-en-2-yl)methyl]-1,2-dimethylimidazol-3-ium
hexafluorophosphate ([N1-dMIm][PF6]) was synthesized
as described by Njoroge et al.2 (link)
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4

Organometallic Heterocycle Synthesis

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Furan, maleic anhydride, 3-bromopropylamine hydrobromide, 1-bromohexane, 3-aminomethyl pyridine, triphenylphosphine, cysteamine, hydrogen tetrachloroaurate(III), sodium borohydride, ethylvinyl ether, 3-bromopyridine, acetic anhydride, petroleum ether, diethyl ether,
N,N-dimethylformamide (DMF),
N,N-dimethylacetamide (DMAc), dichloromethane (DCM), chloroform, pentane, dimethyl sulfoxide (DMSO) were purchased from Sigma Aldrich and used as received. Ethyl acetate and hexane were distilled by conventional techniques. Grubbs second generation catalyst was purchased from Sigma Aldrich. Grubbs third generation catalyst [(H2-Imes)(3-Br-py)2-(Cl)2Ru=CHPh] was freshly prepared according to the previously reported procedure [38]. Phosphate buffered saline (PBS) was obtained from Sigma Aldrich in tablet form. Mueller–Hinton broth (MHB) and Mueller–Hinton agar (MHA) media (both from Dıfco, BD Diagnostic Systems, United States) were used for microbiological tests.
Staphylococcus aureusATCC 25923 strain and
Escherichia coliATCC 25922 strain were acquired from the department of Molecular Biology and Genetics Department (Yildiz Technical University, Turkey) and used as representative of Gram-positive and Gram-negative bacteria, respectively (ATCC is the registered trademark of American Type Culture Collection).
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