Direct beta-Alkylation of Aldehydes via Photoredox Organocatalysis

作者:Terrett Jack A; Clift Michael D; MacMillan David W C*
来源:Journal of the American Chemical Society, 2014, 136(19): 6858-6861.
DOI:10.1021/ja502639e

摘要

Direct beta-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated beta-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce beta-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.

  • 出版日期2014-5-14