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Issue 21, 2020
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Rhodium-catalyzed tandem acylmethylation/annulation of N-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazole N-oxides

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Abstract

An atom-economical protocol for synthesizing indazole N-oxides from readily available N-nitrosoanilines and sulfoxonium ylides through the rhodium(III)-catalyzed C–H activation and cyclization reaction is described here. This protocol employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate to good yields under an ambient atmosphere, providing a straightforward approach to access structurally diverse and valuable indazole N-oxide derivatives. Importantly, this new annulation process represents a hitherto unobserved reactivity pattern for the N-nitroso group.

Graphical abstract: Rhodium-catalyzed tandem acylmethylation/annulation of N-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazole N-oxides

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Supplementary files

Article information


Submitted
06 Apr 2020
Accepted
12 May 2020
First published
13 May 2020

Org. Biomol. Chem., 2020,18, 4014-4018
Article type
Communication

Rhodium-catalyzed tandem acylmethylation/annulation of N-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazole N-oxides

X. Cui and G. Huang, Org. Biomol. Chem., 2020, 18, 4014
DOI: 10.1039/D0OB00723D

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