Palladium-Catalyzed Cross-Coupling Reactions of Borylated o-Carborane: Synthesis of 3,6-Diaryl-o-carboranes

doi:10.6023/cjoc201805018

Abstract

Palladium catalyzed cross-coupling of 3,6-(Bpin)₂-o-carborane (Bpin=pinacolatoboryl) with aryl bromides has been achieved, leading to the formation of a series of B(3,6)-diarylated-o-carborane derivatives in moderate yields. In this reaction, PdCl₂(cod)/tricyclohexylphosphine was used as catalyst to avoid the formation of palladium-catalyzed aryl-aryl exchange and direct B-H arylation by-products. A possible mechanism is proposed, involving a tandem sequence of oxidative addition, anion exchange, transmetalation, and reductive elimination.

Key words: carborane, coupling reaction, palladium, carboranyl boronate, aryl bromide

Cite this article

Xu Xinbin, Cheng Ruofei, Qiu Zaozao, Pan Chengling. Palladium-Catalyzed Cross-Coupling Reactions of Borylated o-Carborane: Synthesis of 3,6-Diaryl-o-carboranes[J]. Chin. J. Org. Chem., 2018, 38(11): 3078-3085.

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