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trans-Chloro(1-Naphthyl)bis(triphenylphosphine)nickel(II)/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates at Room Temperature

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journal contribution
posted on 16.03.2012, 00:00 authored by Pawaret Leowanawat, Na Zhang, Mehtap Safi, David J. Hoffman, Miriam C. Fryberger, Aiswaria George, Virgil Percec
trans-Chloro­(1-naphthyl)­bis­(triphenylphosphine)­nickel­(II) complex/PCy3 system has been successfully applied as catalyst for the Suzuki–Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni­(II)-based catalyst can be utilized as an alternative to Ni­(COD)2/PCy3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.