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Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes

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Abstract

Transition-metal-catalyzed directed C–H functionalization has emerged as a powerful and straightforward tool to construct C–C bonds and C–N bonds. Among these processes, the intramolecular annulative alkene hydroarylation reaction has received much attention because this intramolecular annulation can produce more complex and high value-added structural motifs found in numerous natural products and bioactive molecules. Despite remarkable progress, these annulative protocols developed to date remain limited to hydroarylation and functionalization of one side of alkenes, thus largely limiting the structural diversity and complexity. Herein, we developed a rhodium(III)-catalyzed tandem annulative arylation/amidation reaction of aromatic tethered alkenes to deliver a variety of 2,3-dihydro-3-benzofuranmethanamine derivatives bearing an all-carbon quaternary stereo center by employing 3-substituted 1,4,2-dioxazol-5-ones as an amidating reagent to capture the transient C(sp3)–Rh intermediate. Notably, by simply changing the directing group, a second, unsymmetrical ortho C–H amidation/annulation can be achieved to provide tricyclic dihydrofuro[3,2-f]quinazolinones in good yields.

Graphical abstract: Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes

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Article information


Submitted
22 Jul 2020
Accepted
28 Sep 2020
First published
16 Oct 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Rh(III)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes

C. Chen, C. Shi, Y. Yang and B. Zhou, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC04007J

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