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

Ramendra Pratap; Hideki Yorimitsu

doi:10.1055/s-0037-1611732

Synthesis, Table of Contents

Synthesis 2019; 51(13): 2705-2712
DOI: 10.1055/s-0037-1611732

special topic

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

Ramendra Pratap

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan Email: yori@kuchem.kyoto-u.ac.jp

^bDepartment of Chemistry, University of Delhi, North Campus, Delhi, 110007, India

,

Hideki Yorimitsu *

^aDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan Email: yori@kuchem.kyoto-u.ac.jp

› Author Affiliations

Abstract

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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.

Key words

amination - palladium - cross-coupling - organosulfur compounds

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References

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