Issue 2, 2017

Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis

Abstract

A novel and straightforward strategy for functionalized 1H-indazoles is realized by the Rh(III)-catalyzed double C–H activation and C–H/C–H cross coupling of readily available aldehyde phenylhydrazones. The reaction is scalable and various 1H-indazoles could be afforded in moderate to high yields with good functional-group compatibility. Mechanism experiments and DFT calculations suggest the distinctive Rh(III)-catalyzed C–H/C–H cross coupling reaction underwent a cascade C(aryl)–H bond metalation, C(aldhyde)–H bond insertion and reductive elimination process.

Graphical abstract: Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis

Supplementary files

Article information

Article type
Edge Article
Submitted
31 8 2016
Accepted
06 10 2016
First published
07 10 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 1303-1308

Rh(III)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis

P. Xu, G. Wang, Z. Wu, S. li and C. Zhu, Chem. Sci., 2017, 8, 1303 DOI: 10.1039/C6SC03888C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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