Issue 10, 2016

Versatile and highly efficient oxidative C(sp3)–H bond functionalization of tetrahydroisoquinoline promoted by bifunctional diethyl azodicarboxylate (DEAD): scope and mechanistic insights

Abstract

Oxidative C(sp3)–H bond functionalization of the 1-position of tetrahydroisoquinoline (THIQ) derivatives was performed by using diethyl azodicarboxylate (DEAD) as the oxidant. A wide range of nucleophiles, including ketene silyl acetal, silyl enol ether, nitroalkane, dimethyl malonate, terminal alkyne, ketone, phosphonate, trimethylsilyl cyanide, and allylstannane gave very high yields without their excessive use. A mechanistic study revealed that the oxidative and basic nature of DEAD is responsible for its high efficiency.

Graphical abstract: Versatile and highly efficient oxidative C(sp3)–H bond functionalization of tetrahydroisoquinoline promoted by bifunctional diethyl azodicarboxylate (DEAD): scope and mechanistic insights

Supplementary files

Article information

Article type
Research Article
Submitted
05 Jun 2016
Accepted
28 Jul 2016
First published
01 Aug 2016

Org. Chem. Front., 2016,3, 1259-1264

Versatile and highly efficient oxidative C(sp3)–H bond functionalization of tetrahydroisoquinoline promoted by bifunctional diethyl azodicarboxylate (DEAD): scope and mechanistic insights

T. Suga, S. Iizuka and T. Akiyama, Org. Chem. Front., 2016, 3, 1259 DOI: 10.1039/C6QO00249H

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