Synthesis 2017; 49(21): 4731-4737
DOI: 10.1055/s-0036-1589018
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© Georg Thieme Verlag Stuttgart · New York

Synthetic Access to 3,5,7-Trisubstituted Indoles Enabled by Iridium­-Catalyzed C–H Borylation

Andrew S. Eastabrook
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Further Information

Publication History

Received: 13 March 2017

Accepted after revision: 10 April 2017

Publication Date:
08 May 2017 (eFirst)

Published as part of the Special Topic Modern Strategies for Borylation in Synthesis

Abstract

A one-pot conversion of 3-substituted indoles into their 5,7-diboryl derivatives is reported. The simultaneous functionalization of the C5-H and C7-H sites is achieved using an iridium-catalyzed triborylation-protodeborylation sequence. The 5,7-diborylindoles are useful intermediates that can be readily derivatized into a variety of indoles possessing the rare 3,5,7-trisubstitution pattern, including the natural product (+)-plakohypaphorine C.

Supporting Information

 
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