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Angew Chem Int Ed Engl. 2017 Mar 1;56(10):2749-2753. doi: 10.1002/anie.201611809. Epub 2017 Jan 27.

Highly para-Selective C-H Alkylation of Benzene Derivatives with 2,2,2-Trifluoroethyl α-Aryl-α-Diazoesters.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, China.

Abstract

Compared to the most popular directing-group-assisted strategy, the "undirected" strategy for C-H bond functionalization represents a more flexible but more challenging approach. Reported herein is a gold-catalyzed highly site-selective C(sp2 )-H alkylation of unactivated arenes with 2,2,2-trifluoroethyl α-aryl-α-diazoesters. This protocol demonstrates that high site-selective C-H bond functionalization can be achieved without the assistance of a directing group. In this transformation, both the gold catalyst and trifluoroethyl group on the ester of the diazo compound play vital roles for achieving the chemo- and regioselectivity.

KEYWORDS:

C−H activation; arenes; diazo compounds; gold; homogeneous catalysis

PMID:
28128509
DOI:
10.1002/anie.201611809

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