Direct β-alkylation of aldehydes via photoredox organocatalysis

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[1] Terrett, Jack A.
[2] Clift, Michael D.
[3] MaCmillan, David W. C.
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MaCmillan, D.W.C. (dmacmill@princeton.edu) | 1600年 / American Chemical Society卷 / 136期
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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. © 2014 American Chemical Society;
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