4.8 Article

Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions

Journal

ORGANIC LETTERS
Volume 21, Issue 4, Pages 974-979

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03957

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Funding

  1. National Key R&D Program of China [2016YFA0202902]
  2. National Natural Science Foundation of China [21572036, 21871059, 21801040, 21861132002]
  3. Youth Foundation of Jiangxi Educational Committee [GJJ170432]
  4. Department of Chemistry at Fudan University

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A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal -catalyzed two-component coupling systems, the sterically hindered aryl groups in diaryliodonium salts are preferentially transferred over less bulky ones to form synthetically difficult targets, including those of pharmaceutical importance.

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