Issue 24, 2022

RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group

Abstract

Rhodium-catalyzed diverse tandem twofold C–H bond activation reactions of para-olefin-tethered arenes have been realized, with unsaturated reagents such as internal alkynes, dioxazolones, and isocyanates being the coupling partner as well as a relay directing group which triggers cyclization of the para-olefin group under oxidative or redox-neutral conditions. The reaction proceeded via initial ortho-C–H activation assisted by a built-in directing group in the arene, and the ortho-incorporation of the unsaturated coupling partner simultaneously generated a relay directing group that allows sequential C–H activation at the meta-position and subsequent cyclization of the para-olefins. The overall reaction represents C–C or N–C difunctionalization of the arene with the generation of diverse 2,3-dihydrobenzofuran platforms. The catalytic system proceeded with good efficiency, simple reaction conditions, and broad substrate scope. The diverse transformations of the products demonstrated the synthetic utility of this tandem reaction.

Graphical abstract: RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group

Supplementary files

Article information

Article type
Edge Article
Submitted
19 Apr 2022
Accepted
28 May 2022
First published
30 May 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 7347-7354

RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group

L. Sun, Y. Zhao, B. Liu, J. Chang and X. Li, Chem. Sci., 2022, 13, 7347 DOI: 10.1039/D2SC02205B

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