4.8 Article

New Design of a Disulfurating Reagent: Facile and Straightforward Pathway to Unsymmetrical Disulfanes by Copper-Catalyzed Oxidative Cross-Coupling

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 45, Pages 14121-14125

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608011

Keywords

copper; cross-coupling; disulfuration; sulfur; synthetic methods

Funding

  1. NSFC [21672069, 21472050, 21272075]
  2. DFMEC [20130076110023]
  3. Fok Ying Tung Education Foundation [141011]
  4. Program for Shanghai Rising Star [15QA1401800]
  5. Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
  6. National Program for Support of Top-notch Young Professionals

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A novel reagent, which introduces two sulfur atoms in one step, was designed and used for the construction of diverse disulfanes by copper-catalyzed oxidative cross-coupling under mild reaction conditions. By applying this stable and readily prepared reagent, late-stage modification of pharmaceuticals and natural products can be achieved straightforward. The scaled-up experiments further indicated the practicality of this protocol. The pHvalue of the system plays a key role in achieving highly selective cleavage of the C-S bond instead of a S-S bond in the transformation.

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