A copper-mediated oxidative coupling route to 3H- and 1H-indoles from N-aryl-enamines

TY - JOUR

T1 - A copper-mediated oxidative coupling route to 3H- and 1H-indoles from N-aryl-enamines

AU - Drouhin, Pauline

AU - Taylor, Richard J. K.

PY - 2015/4

Y1 - 2015/4

N2 - A facile copper(II)-mediated C-H bond oxidation and C-C bond formation procedure has been applied to the synthesis of indole derivatives. Intramolecular oxidative coupling of 3,3-disubstituted enamines proceeded using a non-expensive and air-stable copper salt, Cu(2-ethylhexanoate)2, to afford the corresponding C-3 quaternary indolenine products in good to excellent yields. 1H-Indoles can be prepared in a similar manner but in this case, Cu(OAc)2·H2O has been found to be the preferred oxidant.

AB - A facile copper(II)-mediated C-H bond oxidation and C-C bond formation procedure has been applied to the synthesis of indole derivatives. Intramolecular oxidative coupling of 3,3-disubstituted enamines proceeded using a non-expensive and air-stable copper salt, Cu(2-ethylhexanoate)2, to afford the corresponding C-3 quaternary indolenine products in good to excellent yields. 1H-Indoles can be prepared in a similar manner but in this case, Cu(OAc)2·H2O has been found to be the preferred oxidant.

KW - 1H-Indole

KW - 3H-Indole

KW - Copper-mediated coupling

KW - Cyclization

KW - Heterocycles

UR - http://www.scopus.com/inward/record.url?scp=84926657466&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201500112

DO - 10.1002/ejoc.201500112

M3 - Article

AN - SCOPUS:84926657466

SN - 1434-193X

VL - 2015

SP - 2333

EP - 2336

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 11

ER -