Engaging Alkenes and Alkynes in Deaminative Alkyl-Alkyl and Alkyl-Vinyl Cross-Couplings of Alkylpyridinium Salts

Kristen M. Baker, Diana Lucas Baca, Shane Plunkett, Mitchell E. Daneker and Mary P. Watson*

*Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email: mpwatsonudel.edu

K. M. Baker, D. L. Baca, S. Plunkett, M. E. Daneker, M. P. Watson, Org. Lett., 2019, 21, 9738-9741.

DOI: 10.1021/acs.orglett.9b03899

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Abstract

An alkyl-alkyl cross-coupling of organoboranes, formed in situ via hydroboration of alkenes, and Katritzky alkylpyridinium salts has been developed. Under the mild reaction conditions, a broad range of functional groups, including protic groups, is tolerated. The strategy is also effective with alkynes, enabling a C(sp³)-C(sp²) cross-coupling.

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Key Words

alkyl-alkyl cross-coupling, alkylation of carbonyl compounds

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ID: J54-Y2019