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N butyllithium

Manufactured by Kanto Chemical

N-butyllithium is a colorless, flammable, pyrophoric organometallic compound. It is a strong base used as a reagent in organic synthesis for the preparation of other organolithium compounds.

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2 protocols using n butyllithium

1

Synthesis of Functionalized Alkyne Monomers

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Bis(triphenylphosphine)palladium(ii) dichloride, triphenylphosphine, copper(i) iodide, 1-bromo-4-tert-butylbenzene, 1,4-dibromobenzene, sodium hydride, iodomethane, 2-methyl-3-butyn-2-ol, tetrahydrofuran (THF), triethylamine, N,N-dimethylformamide (DMF), chloroform (CHCl3), methanol (MeOH), trifluoroacetic acid (TFA), dimethyl sulfoxide (DMSO) (Fujifilm Wako Pure Chemical (Wako)), chlorotrimethylsilane (Tokyo Chemical Industry), n-butyllithium (Kanto Chemical), tantalum(v) chloride, and phenylacetylene (Sigma-Aldrich) were used without additional purification. n-Bu4Sn (cocatalyst for polymerization, Wako) and toluene (solvent for polymerization, Wako) were distilled over CaH2 (Wako) prior to use. 1-(p-Trimethylsilyl)phenyl-1-propyne (SPP),21 (link) 4-(tert-butyl)diphenylacetylene (BDPA),10 (link) and 4-(trimethylsilyl)diphenylacetylene (SDPA)11 (link) were prepared according to the literature.
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2

Synthesis and Characterization of Copper(II) Complexes

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The reactions were monitored by
TLC using Merck “Aluminum oxide 60 F254 neutral,
aluminum sheets” and Merck “Silica gel 60 F254, aluminum sheets”. Column chromatography was carried out
with the use of Al2O3 (Alumina activated 300,
Nacalai Tesque). The reagents used without additional purification
included 2-bromo-3-formylpyridine (96%, Sigma-Aldrich), 5-bromonicotinaldehyde
(97%, Sigma-Aldrich), 6-bromo-3-formylpyridine (95%, Sigma-Aldrich),
3-bromo-2-methylpyridine (97%, Sigma-Aldrich), 3-bromo-5-methylpyridine
(97%, Sigma-Aldrich), 5-bromo-2-methylpyridine (99%, Sigma-Aldrich), n-butyllithium (1.6 M in n-hexane, Kanto
Chemical Co., INC), ethyl formate (FUJIFILM Wako Pure Chemical Corporation),
and PbO2 (FUJIFILM Wako Pure Chemical Corporation). Cu(hfac)2,33 (link) 2,3-bis(hydroxyamino)-2,3-dimethylbutane,34 (link) and 2-methylnicotin aldehyde, 5-methylnicotin
aldehyde, and 6-methylnicotin aldehyde35 were synthesized by standard procedures. C, H, and N elemental analyses
were carried out on a 2400 CHNS/O Series II System (100V) analyzer.
Thermogravimetric and differential thermal analysis (TG-DTA) for polycrystalline
samples [Cu(hfac)2L5-Me]2, [Cu(hfac)2L5-Br]2, and [Cu(hfac)2L6-Me]2 was performed using SII EXSTAR TGA operating
under dry nitrogen with heating from 300 to 500 K at a rate of 5 K/min.
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