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Rh-Catalyzed nitrene alkyne metathesis/formal C–N bond insertion cascade: synthesis of 3-iminoindolines

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Abstract

A Rh2(esp)2 catalyzed nitrene/alkyne metathesis (NAM) cascade reaction of alkyne-tethered sulfamates has been developed, which provides facile access to the tricyclic 3-iminoindolines in good to excellent yields with broad substrate scope. The reaction is initiated by a Rh-promoted nitrene/alkyne metathesis (NAM) under oxidative conditions to form the key α-imino metal carbene intermediate, followed by a formal carbene insertion reaction of the amide C–N bond via a Stevens [1,2]-acyl shift.

Graphical abstract: Rh-Catalyzed nitrene alkyne metathesis/formal C–N bond insertion cascade: synthesis of 3-iminoindolines

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Article information


Submitted
07 Mar 2020
Accepted
03 Apr 2020
First published
08 Apr 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Rh-Catalyzed nitrene alkyne metathesis/formal C–N bond insertion cascade: synthesis of 3-iminoindolines

K. Hong, S. Zhou, W. Hu and X. Xu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00294A

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