Synthesis 2017; 49(07): 1680-1688
DOI: 10.1055/s-0036-1588919
paper
© Georg Thieme Verlag Stuttgart · New York

Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki–Miyaura Cross-Coupling in Neat Water

Ksenia V. Kutonova
a  Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation
,
Nicole Jung
b  Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Email: braese@kit.edu
c  Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
,
Marina E. Trusova
a  Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation
,
Victor D. Filimonov
a  Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation
,
Pavel S. Postnikov*
d  Department of Technology of Organic substances and Polymer materials, National Research Tomsk Polytechnic University, 634050 Tomsk, Russian Federation   Email: postnikov@tpu.ru
,
Stefan Bräse*
b  Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Email: braese@kit.edu
c  Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
› Author Affiliations
Further Information

Publication History

Received: 28 October 2016

Accepted after revision: 31 October 2016

Publication Date:
29 November 2016 (online)


Abstract

A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki–Miyaura cross-coupling­ was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.

Supporting Information

 
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