Communication

Palladium-Catalyzed Intermolecular Coupling of 2-Silylaryl Bromides with Alkynes: Synthesis of Benzosiloles and Heteroarene-Fused Siloles by Catalytic Cleavage of the C(sp3)[BOND]Si Bond†

  1. Dr. Yun Liang1,2,
  2. Weizhi Geng1,
  3. Junnian Wei1,
  4. Prof. Dr. Zhenfeng Xi1,3,*

Article first published online: 17 JAN 2012

DOI: 10.1002/anie.201108154

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 8, pages 1934–1937, February 20, 2012

Additional Information

How to Cite

Liang, Y., Geng, W., Wei, J. and Xi, Z. (2012), Palladium-Catalyzed Intermolecular Coupling of 2-Silylaryl Bromides with Alkynes: Synthesis of Benzosiloles and Heteroarene-Fused Siloles by Catalytic Cleavage of the C(sp3)[BOND]Si Bond. Angew. Chem. Int. Ed., 51: 1934–1937. doi: 10.1002/anie.201108154

Author Information

  1. 1

    Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular, Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China)

  2. 2

    Key Laboratory of Resource Fine-Processing and Advanced, Materials of Hunan Province, Key Laboratory of Chemical, Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081 (China)

  3. 3

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032 (China)

*Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular, Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China)

  1. †

    This work was supported by the Natural Science Foundation of China and the 973 Program (2012CB821603).

Publication History

  1. Issue published online: 14 FEB 2012
  2. Article first published online: 17 JAN 2012
  3. Manuscript Received: 21 NOV 2011

Funded by

  • Natural Science Foundation of China
  • 973 Program. Grant Number: 2012CB821603

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (368K)

Keywords:

  • cleavage reactions;
  • C[BOND]Si activation;
  • intermolecular coupling;
  • palladium;
  • trialkylsilyl group
Thumbnail image of graphical abstract

Unusual split: A wide variety of benzosiloles and derivatives are obtained by the Pd-catalyzed intermolecular coupling of 2-silylaryl bromides and alkynes and the accompanying selective cleavage of the C(sp3)[BOND]Si bonds as a key step (see scheme). The product spectrum includes benzosiloles, benzothiophene-fused siloles, ladder-type π-conjugated benzosiloles, and thiophene-bridged 2,5-bisbenzosiloles.

View Full Article with Supporting Information (HTML) Get PDF (368K)