Issue 9, 2022

Rh(iii)-Catalyzed C–H bond activation/annulation reactions of arylacyl ammonium salts with 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones

Abstract

Herein, we report a C–H bond functionalization strategy for the construction of oxo- and aza-spirocyclic compounds from diazo compounds as coupling partners. Our method comprises ortho sp2 C–H bond activation of arylacyl ammonium salts, followed by coupling with two types of cyclic diazo compounds i.e. 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones, respectively. The mechanism involves the formation of dual metal carbene intermediates in situ with the breakage of oxidizing C–N bonds in arylacyl ammonium salts. The cascade C–H activation/annulation process gave a variety of novel spiro[indene-1,4′-isochromane]-3,3′(2H)-diones and spiro[indene-1,4′-isoquinoline]-3,3′(2H)-diones in good to excellent yields. Readily available starting materials, broad substrate scope, and operationally simple and mild reaction conditions are the prominent features of this method.

Graphical abstract: Rh(iii)-Catalyzed C–H bond activation/annulation reactions of arylacyl ammonium salts with 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones

Supplementary files

Article information

Article type
Paper
Submitted
09 Dec 2021
Accepted
09 Feb 2022
First published
09 Feb 2022

Org. Biomol. Chem., 2022,20, 1900-1906

Rh(III)-Catalyzed C–H bond activation/annulation reactions of arylacyl ammonium salts with 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones

M. Suleman, M. Qi, J. Xie, P. Lu and Y. Wang, Org. Biomol. Chem., 2022, 20, 1900 DOI: 10.1039/D1OB02405A

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