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J Org Chem. 2012 Apr 6;77(7):3543-8. doi: 10.1021/jo202472k. Epub 2012 Mar 20.

Carbon-boron bond cross-coupling reaction catalyzed by -PPh(2) containing palladium-indolylphosphine complexes.

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State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong.


This study describes the application of indolylphosphine ligands with a diphenylphosphino moiety to the palladium-catalyzed borylation of aryl chlorides. The combination of palladium metal precursor with PPh(2)-Andole-phos, which comprises an inexpensive -PPh(2) group, provides highly effective catalysts for the borylation of aryl chlorides. A range of functional groups such as -CN, -NO(2), -CHO, -COMe, -COOMe, and -CF(3) was compatible, and the catalyst loading down to 0.025 mol % of Pd can be achieved. The Pd/PPh(2)-Andole-phos system is able to catalyze both borylation reaction and Suzuki-Miyaura coupling reaction in a one-pot sequential manner for the direct synthesis of biaryl compounds in excellent yields.

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