Issue 60, 2016

Gold-catalysed facile access to indene scaffolds via sequential C–H functionalization and 5-endo-dig carbocyclization

Abstract

A concise synthesis of functionalized indene derivatives via the gold(I)-catalysed cascade C–H functionalization/conia-ene type reaction of electron-rich aromatics with o-alkynylaryl α-diazoesters has been developed. In this transformation, the gold catalyst not only catalysed the formation of the zwitterionic intermediate via intermolecular C–H functionalization but promoted the subsequent intramolecular 5-endo-dig cyclization via activation of alkynes. The reaction is characterized by high chemo- and site-selectivity, readily available starting materials, nice functional-group tolerance and mild reaction conditions.

Graphical abstract: Gold-catalysed facile access to indene scaffolds via sequential C–H functionalization and 5-endo-dig carbocyclization

Supplementary files

Article information

Article type
Communication
Submitted
13 May 2016
Accepted
27 Jun 2016
First published
27 Jun 2016

Chem. Commun., 2016,52, 9351-9354

Gold-catalysed facile access to indene scaffolds via sequential C–H functionalization and 5-endo-dig carbocyclization

B. Ma, Z. Wu, B. Huang, L. Liu and J. Zhang, Chem. Commun., 2016, 52, 9351 DOI: 10.1039/C6CC04034A

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