Financial support from the Major State Basic Research and Development Program (2011CB808700) and the NSF of China (21102164 for the DFT calculation) is acknowledged. We thank G. Chai of our research group for reproducing the results presented in entries 3 and 14 of Table 2.
One-Pot Approach to Installing Eight-Membered Rings onto Indoles†
Article first published online: 27 JUN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 31, pages 7817–7820, July 27, 2012
How to Cite
Zhu, C., Zhang, X., Lian, X. and Ma, S. (2012), One-Pot Approach to Installing Eight-Membered Rings onto Indoles . Angew. Chem. Int. Ed., 51: 7817–7820. doi: 10.1002/anie.201202971
- Issue published online: 25 JUL 2012
- Article first published online: 27 JUN 2012
- Manuscript Revised: 11 MAY 2012
- Manuscript Received: 18 APR 2012
- Major State Basic Research and Development Program. Grant Number: 2011CB808700
- NSF of China. Grant Number: 21102164
Ring fusion: The Pd0-catalyzed reaction of 2-allyl-3-iodo-1-tosyl-1H-indoles and propargylic bromides affords dihydrocycloocta[b]indoles (see scheme; M.S.=molecular sieves, TFP=tris(2-furyl)phosphine, Ts=4-toluenemethanesulfonyl), and proceeds by carbon–carbon coupling, [1,5]-hydrogen migration, and electrocyclization. The newly established method was used to efficiently access iprindole.