TY - JOUR
T1 - Selective Radical-Radical Cross-Couplings
T2 - Design of a Formal β-Mannich Reaction
AU - Jeffrey, Jenna L.
AU - Petronijević, Filip R.
AU - Macmillan, David W.C.
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/7/8
Y1 - 2015/7/8
N2 - A direct β-coupling of cyclic ketones with imines has been accomplished via the synergistic combination of photoredox catalysis and organocatalysis. Transient β-enaminyl radicals derived from ketones via enamine and oxidative photoredox catalysis readily combine with persistent α-amino radicals in a highly selective hetero radical-radical coupling. This novel pathway to γ-aminoketones is predicated upon the use of DABCO as both a base and an electron transfer agent. This protocol also formally allows for the direct synthesis of β-Mannich products via a chemoselective three-component coupling of aryl aldehydes, amines, and ketones.
AB - A direct β-coupling of cyclic ketones with imines has been accomplished via the synergistic combination of photoredox catalysis and organocatalysis. Transient β-enaminyl radicals derived from ketones via enamine and oxidative photoredox catalysis readily combine with persistent α-amino radicals in a highly selective hetero radical-radical coupling. This novel pathway to γ-aminoketones is predicated upon the use of DABCO as both a base and an electron transfer agent. This protocol also formally allows for the direct synthesis of β-Mannich products via a chemoselective three-component coupling of aryl aldehydes, amines, and ketones.
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U2 - 10.1021/jacs.5b05376
DO - 10.1021/jacs.5b05376
M3 - Article
C2 - 26075347
AN - SCOPUS:84936817326
VL - 137
SP - 8404
EP - 8407
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 26
ER -