4.7 Article

Boron-promoted reductive deoxygenation coupling reaction of sulfonyl chlorides for the C(sp3)-S bond construction

Journal

CHINESE CHEMICAL LETTERS
Volume 33, Issue 12, Pages 5101-5105

Publisher

ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2022.04.022

Keywords

C-S bond formation; Reductive deoxygenation coupling; Borane; Organosulfur compounds; Green chemistry

Funding

  1. Natural Science Foundation of Sichuan [2021YJ0413]
  2. Sichuan Key Laboratory of Medical Imaging (North Sichuan Medical College) [SKLMI201901]
  3. Strategic Cooperation of Science and Technology between Nanchong City and North Sichuan Medical College [19SXHZ0441, 19SXHZ0227]
  4. Chongqing Postdoctoral Science Foundation [cstc2020jcyj-bshX0052]
  5. China Postdoctoral Science Foundation [2020M673121]

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A borane-promoted reductive deoxygenation coupling reaction for synthesizing sulfides is reported. The reaction shows excellent substrate scope and high efficiency, making it suitable for late-stage functionalization of biomolecules.
Herein, we report a borane-promoted reductive deoxygenation coupling reaction to synthesize sulfides. This reaction features excellent functional group compatibility, high efficiency, broad substrate scope, and application in late-stage functionalization of biomolecules. Preliminary mechanistic studies suggest di-aryl sulfides are the intermediates of this reaction. Moreover, the real active aryl sulfide anions may be generated in situ with the aid of B(2)pin(2) and react with alkyl tosylates through a concerted S(N)2 pathway. (c) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

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