Issue 20, 2020

Rhenium-catalyzed alkylarylation of alkenes with PhI(O2CR)2via decarboxylation to access indolinones and dihydroquinolinones

Abstract

Rhenium-catalyzed alkylarylation of alkenes with hypervalent iodine(III) reagents (HIRs) via decarboxylation to access various 3,3-disubstituted indolinones and trans-3,4-dihydroquinolinones is described. These transformations feature wide substrate scopes, good functional-group tolerance, and divergent regioselectivity. Mechanistic studies revealed a cascade sequence of decarboxylation/intermolecular radical alkylation/intramolecular radical arylation/oxidative re-aromatization.

Graphical abstract: Rhenium-catalyzed alkylarylation of alkenes with PhI(O2CR)2via decarboxylation to access indolinones and dihydroquinolinones

Supplementary files

Article information

Article type
Research Article
Submitted
10 Aug 2020
Accepted
11 Sep 2020
First published
14 Sep 2020

Org. Chem. Front., 2020,7, 3234-3241

Rhenium-catalyzed alkylarylation of alkenes with PhI(O2CR)2via decarboxylation to access indolinones and dihydroquinolinones

L. Zhang, Y. Wang, Y. Yang, P. Zhang and C. Wang, Org. Chem. Front., 2020, 7, 3234 DOI: 10.1039/D0QO00953A

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