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

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

Andrew S. Eastabrook, Jonathan Sperry*
  • School of Chemical Sciences, 23 Symonds Street, University of Auckland, Auckland, New Zealand   Email: j.sperry@auckland.ac.nz
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