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

Zdravko Džambaski; Bojan P. Bondžić

doi:10.1039/C9OB01090D

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

Zdravko Džambaski^a and Bojan P. Bondžić

*^a

Author affiliations

* Corresponding authors

^a Center for Chemistry, ICTM institute, University of Belgrade, Njegoševa 12, 11 000 Belgrade, Serbia
E-mail: bbondzic@chem.bg.ac.rs

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.

This article is part of the themed collections: Synthetic methodology in OBC and Direct C-H Functionalization in Method Development and Late Stage Functionalization

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Article information

DOI: https://doi.org/10.1039/C9OB01090D
Article type: Paper
Submitted: 10 May 2019
Accepted: 17 Jun 2019
First published: 18 Jun 2019

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

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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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Organic & Biomolecular Chemistry