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

Lei Zhang; Yin Wang; Yunhui Yang; Ping Zhang; Congyang Wang

doi:10.1039/D0QO00953A

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

Lei Zhang,^ab Yin Wang,^bc Yunhui Yang,^bc Ping Zhang^a and Congyang Wang

*^bcd

Author affiliations

* Corresponding authors

^a National Demonstration Center for Experimental Chemistry Education, Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024, China

^b Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
E-mail: wangcy@iccas.ac.cn

^c University of Chinese Academy of Sciences, Beijing 100049, China

^d Physical Science Laboratory, Huairou National Comprehensive Science Center, Beijing 101400, China

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.

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Article information

DOI: https://doi.org/10.1039/D0QO00953A
Article type: Research Article
Submitted: 10 Aug 2020
Accepted: 11 Sep 2020
First published: 14 Sep 2020

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

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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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