Synthesis 2019; 51(13): 2705-2712
DOI: 10.1055/s-0037-1611732
special topic
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Amination of Aryl Sulfides and Sulfoxides with Azaarylamines of Poor Nucleophilicity

Ramendra Pratap
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
b  Department of Chemistry, University of Delhi, North Campus, Delhi, 110007, India
,
a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
› Author Affiliations
This work was supported by JSPS KAKENHI Grant Numbers JP16H04109, JP18H04252, and JP18H04409. R.P. acknowledges the award of a JSPS Invitational Fellowship.
Further Information

Publication History

Received: 22 December 2018

Accepted after revision: 18 January 2019

Publication Date:
26 February 2019 (online)

Published as part of the Special Topic Amination Reactions in Organic Synthesis

Abstract

The amination of aryl sulfides and sulfoxides with azaarylamines is investigated using a palladium-N-heterocyclic carbene (NHC) complex. Because azaarylamines are less nucleophilic than anilines, more reactive diaryl sulfides and sulfoxides are found to be suitable coupling partners that liberate better leaving arenethiolate or arenesulfenate anions, instead of aryl methyl sulfides as reported previously.

Supporting Information

 
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