Two nickel based catalytic systems, namely Ni(COD)2/PCy3  and trans-chloro(1-naphthyl)bis(triphenylphosphine) nickel(II) complex/PCy3 that catalyze the cross-coupling of aryl and heteroaryl neopentylglycolboronate with aryl and heteroaryl mesylates and sulfamates in THF at room temperature in good to excellent yields were reported. Various functional groups on the aryl electrophile, such as keto, imino, ester, ether and cyano, are tolerated. Ni(COD)2/PCy3 catalytic system showed higher reactivity than trans-chloro(1-naphthyl)bis(triphenylphosphine) nickel(II) complex/PCy3 system for cross-coupling of aryl and heteroaryl sulfamates. However, trans-chloro(1-naphthyl)bis(triphenylphosphine) nickel(II) complex is an inexpensive, easily prepared, and bench-stable alternative to Ni(COD)2. In combination with one-pot, two-step neopentylglycolborylation, these two catalytic systems can be applied to the synthesis of biaryl and heteroaryl compounds.

Nickel catalyzed cross-coupling of aryl and heteroaryl neopentylglycolbronates with aryl and heteroaryl mesylates and sulfamates at room temperature

244th National Meeting (2012)

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