Open AccessEngaging Alkenes and Alkynes in Deaminative Alkyl–Alkyl and Alkyl–Vinyl Cross-Couplings of Alkylpyridinium Salts
Author(s) -
Kristen M. Baker,
Diana Lucas Baca,
Shane Plunkett,
Mitchell E Daneker,
Mary P. Watson
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03899
Subject(s) - chemistry , alkyl , hydroboration , amine gas treating , organic chemistry , medicinal chemistry , catalysis
An alkyl-alkyl cross-coupling of Katritzky alkylpyridinium salts and organoboranes, formed in situ via hydroboration of alkenes, has been developed. This method utilizes the abundance of both alkyl amine precursors and alkenes to form C(sp 3 )-C(sp 3 ) bonds. This strategy is also effective with alkynes, enabling a C(sp 3 )-C(sp 2 ) cross-coupling. Under these mild conditions, a broad range of functional groups, including protic groups, is tolerated. As seen with previous alkylpyridinium cross-couplings, mechanistic studies support an alkyl radical intermediate.