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Photoredox/Nickel Dual Catalytic Cross-Coupling of Potassium Thiomethyltrifluoroborates with Aryl and Heteroaryl Bromides. 2021

Katherine Townsend, and Malcolm P Huestis, and John C Tellis
Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.

The cross-coupling of S-aryl and S-alkyl potassium thiomethyltrifluoroborates with aryl and heteroaryl bromides is reported via photoredox/nickel dual catalysis. The transformation is achieved under mild conditions with commercially available or readily prepared, air stable reagents and affords benzylthioether products in moderate to good yields with good functional group tolerance. A practical and improved synthesis of potassium thiomethyltrifluoroborates is also reported that affords access to previously undescribed reagents.

UI MeSH Term Description Entries
D009532 Nickel A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D011188 Potassium An element in the alkali group of metals with an atomic symbol K, atomic number 19, and atomic weight 39.10. It is the chief cation in the intracellular fluid of muscle and other cells. Potassium ion is a strong electrolyte that plays a significant role in the regulation of fluid volume and maintenance of the WATER-ELECTROLYTE BALANCE.
D001965 Bromides Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Bromide
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses

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