Synthesis of Novel Bromodifluoromethyl(arylsulfonyl) Compounds and Nickel Catalyzed Cross Coupling with Arylboronic Acids

Drug Discovery Summit, Berlin, 2016, Dr. Donald Bierer, Bayer Pharma AG

Synthesis of Novel Bromodifluoromethyl(arylsulfonyl) Compounds and Nickel Catalyzed Cross Coupling with Arylboronic Acids

A nickel catalyzed Suzuki coupling of arylboronic acids and novel bromodifluoromethyl(arylsulfonyl)
compounds is described, providing an example of direct Csp2-CF2SO2Ar bond formation. High-throughput
experimentation (HTE) was utilized for identifying the catalyst and reaction conditions.

• Prepared two novel bromodifluoromethyl(arylsulfonyl) compounds
• Using high-throughput experimentation (HTE) we have identified a very challenging Suzuki type coupling reaction catalyzed by nickel, providing direct formation of C_sp2-CF₂SO₂Ar bonds
• We propose a CF₂SO₂Ar radical species is involved in the reaction pathway
• Future work will focus on the use of a photocatalyst to improve the harsh conditions of this transformation

Graham M. Lee^†§, René Loechtefeld^§, Richard Menssen^§, Donald E. Bierer^§, Bernd Riedl^§, R. Tom Baker^†
†Department of Chemistry and Biomolecular Sciences and Centre for Catalysis Research and Innovation,
University of Ottawa, 30 Marie Curie, Ottawa, Ontario K1N 6N5, Canada
^§Bayer Pharma AG, Medicinal Chemistry Department, Aprather Weg 18A, 42096, Wuppertal, Germany
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