Issue 26, 2019

Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions

Abstract

The organocatalyzed Mannich reaction of unsubstituted and N-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N-aryl-substituted THIQs through dehydrogenative C(sp3)–H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C–H oxidation/Mannich reaction of less reactive N-aryl substituted pyrrolidines is achieved via metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.

Graphical abstract: Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions

Supplementary files

Article information

Article type
Paper
Submitted
10 মে 2019
Accepted
17 জুন 2019
First published
18 জুন 2019

Org. Biomol. Chem., 2019,17, 6420-6425

Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions

Z. Džambaski and B. P. Bondžić, Org. Biomol. Chem., 2019, 17, 6420 DOI: 10.1039/C9OB01090D

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