钯催化硼基化邻-碳硼烷偶联反应制备3,6-双芳基-邻-碳硼烷

doi:10.6023/cjoc201805018

摘要/Abstract

钯催化碳硼烷基-3，6-二硼酸频哪醇酯与芳基溴化物反应，以中等的收率得到一系列硼顶点取代的3，6-双芳基-邻-碳硼烷.反应中使用（1，5-环辛二烯）二氯化钯/三环己基膦作为催化体系，可以避免钯催化芳基-芳基交换及直接硼氢键芳基化的副产物生成.反应路径包括氧化加成、离子交换、转金属以及还原消除过程.

关键词: 碳硼烷, 偶联反应, 钯, 碳硼烷基硼酸酯, 芳基溴化物

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

引用此文

许新彬, 程若飞, 邱早早, 潘成岭. 钯催化硼基化邻-碳硼烷偶联反应制备3,6-双芳基-邻-碳硼烷[J]. 有机化学, 2018, 38(11): 3078-3085.

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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