Issue 32, 2023

Rhodium-catalyzed annulative approach to N–N axially chiral biaryls via C–H activation and dynamic kinetic transformation

Abstract

N–N axially chiral biaryls represent a rarely explored class of atropisomeric compounds. We hereby report rhodium-catalyzed enantioselective [4 + 2] oxidative annulation of internal alkynes with benzamides bearing two classes of N–N directing groups. The coupling occurs under mild conditions via NH and CH annulation through the dynamic kinetic transformation of the directing group and is highly enantioselective with good functional tolerance. Computational studies of a coupling system at the DFT level has been conducted, and the alkyne insertion was identified as the enantio-determining as well as the turnover-limiting step.

Graphical abstract: Rhodium-catalyzed annulative approach to N–N axially chiral biaryls via C–H activation and dynamic kinetic transformation

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Article information

Article type
Edge Article
Submitted
02 jun 2023
Accepted
13 jul 2023
First published
15 jul 2023
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., 2023,14, 8564-8569

Rhodium-catalyzed annulative approach to N–N axially chiral biaryls via C–H activation and dynamic kinetic transformation

X. Zhu, H. Wu, Y. Wang, G. Huang, F. Wang and X. Li, Chem. Sci., 2023, 14, 8564 DOI: 10.1039/D3SC02800C

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