Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 6, Pages 2257-2262Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b00111
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Funding
- NIH [R01 GM111820, NSF CHE0421224, CHE1229234, CHE0840401, CHE1048367, NIHP 20 GM104316, P20 GM103541, S10 OD016267]
- University of Delaware (UD)
- NSF
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A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the non-canonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance.
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