Issue 33, 2020

l-Proline-catalyzed regioselective C1 arylation of tetrahydroisoquinolines through a multicomponent reaction under solvent-free conditions

Abstract

Here we disclose the C1 arylation of tetrahydroisoquinolines (THIQ) through regioselective C(sp3)–H functionalization using a multicomponent reaction. The reaction was performed by reacting THIQ, aldehydes and aminopyrazoles or indoles under neat conditions with L-proline as a catalyst. The regioselectivity of the products was confirmed by X-ray analysis and spectroscopic data. The formation of an azomethine ylide intermediate is crucial for obtaining the regioselectivity.

Graphical abstract: l-Proline-catalyzed regioselective C1 arylation of tetrahydroisoquinolines through a multicomponent reaction under solvent-free conditions

Supplementary files

Article information

Article type
Communication
Submitted
03 Jul 2020
Accepted
04 Aug 2020
First published
17 Aug 2020

Org. Biomol. Chem., 2020,18, 6514-6518

L-Proline-catalyzed regioselective C1 arylation of tetrahydroisoquinolines through a multicomponent reaction under solvent-free conditions

I. Rahman, B. Deka, R. Thakuria, M. L. Deb and P. K. Baruah, Org. Biomol. Chem., 2020, 18, 6514 DOI: 10.1039/D0OB01363C

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