Synlett 2013; 24(20): 2624-2628
DOI: 10.1055/s-0033-1338981
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© Georg Thieme Verlag Stuttgart · New York

Multidentate Halogen-Bond Donors as Lewis Acidic Activators or Catalysts in Halide Abstraction Reactions

Stefan H. Jungbauer
Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching b. München, Germany   Fax: +49(89)28913315   Email: stefan.m.huber@tum.de
,
Severin Schindler
Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching b. München, Germany   Fax: +49(89)28913315   Email: stefan.m.huber@tum.de
,
Florian Kniep
Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching b. München, Germany   Fax: +49(89)28913315   Email: stefan.m.huber@tum.de
,
Sebastian M. Walter
Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching b. München, Germany   Fax: +49(89)28913315   Email: stefan.m.huber@tum.de
,
Laxmidhar Rout
Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching b. München, Germany   Fax: +49(89)28913315   Email: stefan.m.huber@tum.de
,
Stefan M. Huber*
Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching b. München, Germany   Fax: +49(89)28913315   Email: stefan.m.huber@tum.de
› Author Affiliations
Further Information

Publication History

Received: 07 August 2013

Accepted after revision: 06 September 2013

Publication Date:
28 October 2013 (online)

Abstract

Although halogen bonds share many similarities with hydrogen bonds, they have so far found virtually no application in organic synthesis. This account summarizes our efforts to use multidentate halogen-bond donors (halogen-based Lewis acids) in formal halide abstraction reactions. Following a first proof-of-principle study, we recently reported the first halogen-bond-based organocatalytic carbon–carbon bond-forming reaction.

 
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