Organic Letters
Organic Letters
5 years ago

Photoredox-Catalyzed Cross-Coupling of Enamides for the Assembly of β-Difluoroimine Synthons

Photoredox-Catalyzed Cross-Coupling of Enamides for the Assembly of β-Difluoroimine Synthons
Jian Wang, Jicheng Wu, Ming Lang
A photoredox-catalyzed formal Csp3–Csp3 cross-coupling reaction of enamides with bromodifluoro compounds is established. The resulting gem-difluoromethylenated γ-imines indicated high stability, excellent E/Z control, and broad functional group tolerance. These synthetic intermediates can efficiently transfer to difluoromethylenated γ-amino acids or δ-amino alcohols. Mechanistic analysis indicates that a radical/SET mechanism proceeding via a difluoroalkyl radical may be involved in the catalytic cycle.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02809

DOI: 10.1021/acs.orglett.7b02809

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