Communication

One-Pot Approach to Installing Eight-Membered Rings onto Indoles†

  1. Can Zhu1,
  2. Xue Zhang1,
  3. Xiongdong Lian1,
  4. Prof. Dr. Shengming Ma1,2,*

Article first published online: 27 JUN 2012

DOI: 10.1002/anie.201202971

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 31, pages 7817–7820, July 27, 2012

Additional Information

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

Author Information

  1. 1

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)

  2. 2

    Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P.R. China)

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China)

  1. †

    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.

Publication History

  1. Issue published online: 25 JUL 2012
  2. Article first published online: 27 JUN 2012
  3. Manuscript Revised: 11 MAY 2012
  4. Manuscript Received: 18 APR 2012

Funded by

  • Major State Basic Research and Development Program. Grant Number: 2011CB808700
  • NSF of China. Grant Number: 21102164

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (395K)

Keywords:

  • allenes;
  • cyclization;
  • heterocycles;
  • indium;
  • palladium
Thumbnail image of graphical abstract

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.

View Full Article with Supporting Information (HTML) Get PDF (395K)