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DOI: 10.1055/s-0036-1591243
Expanding Functionality of Indole and Pyrrole the Electrophilic Way
Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung.
Chem. Eur. J. 2017;
DOI: 10.1002/chem.201703723
Publication History
Publication Date:
18 September 2017 (online)
Significance
Indole and pyrrole are common compounds in nature. Their electron-rich character, however, sometimes limits their usefulness for pharmaceutical applications. Here, the authors show that electrophilic indole and pyrrole can be prepared by reaction with benziodoxolones (BX). The indole group in the intermediate is then transferred to form a new C–H bond.
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Comment
The authors present a straightforward way to activate a C–H bond on indole or pyrrole. This has been achieved by using the electron-withdrawing BX group. The indole- and pyrrole-BX compounds were stable up to 150 °C. The Rh- and Ru-catalyzed transfer was versatile, and different length of alkyl chains, methoxy, halogens, esters, cyanide derivatives were obtained in good yield.
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