Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl–Alkyl Cross-Couplings

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 wi...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 6; pp. 2257 - 2262
Main Authors Plunkett, Shane, Basch, Corey H, Santana, Samantha O, Watson, Mary P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.02.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
cross-coupling reactions
halides
Lewis acids
moieties
Physical Sciences
primary amines
Science & Technology
BORONIC ACIDS
AMINO-GROUPS
ESTERS
BOND FUNCTIONALIZATION
SECONDARY
ARYL
PYRIDINIUM SALTS
BENZYLIC AMMONIUM-SALTS
NICKEL-CATALYZED BORYLATION
CARBOXYLIC-ACIDS
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Summary: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 noncanonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance.
Bibliography:NIH RePORTER
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.9b00111