Direct β-Alkylation of Aldehydes via Photoredox Organocatalysis | Zendy

Jack A. Terrett | Zendy; Michael D. Clift | Zendy; David W. C. MacMillan | Zendy

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Direct β-Alkylation of Aldehydes via Photoredox Organocatalysis

Author(s) -

Jack A. Terrett,

Michael D. Clift,

David W. C. MacMillan

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja502639e

Subject(s) - chemistry , organocatalysis , enamine , photoredox catalysis , alkylation , catalysis , alkyl , redox , combinatorial chemistry , photochemistry , michael reaction , quenching (fluorescence) , organic chemistry , enantioselective synthesis , photocatalysis , physics , quantum mechanics , fluorescence

Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.

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