芳基
催化作用
化学
钴
试剂
硼
锂(药物)
反离子
醇盐
有机化学
硼酸化
组合化学
烷基
医学
内分泌学
离子
作者
Sanita B. Tailor,Michela Manzotti,Gavin J. Smith,Sean A. Davis,Robin B. Bedford
标识
DOI:10.1021/acscatal.0c05557
摘要
The cobalt-catalyzed Suzuki biaryl cross-coupling of aryl chloride substrates with aryl boron reagents, activated with more commonly used bases, remained a significant unmet challenge in the race to replace platinum group metal catalysts with Earth-abundant metal alternatives. We now show that this highly desirable process can be realized using alkoxide bases, provided the right counterion is employed, strict stoichiometric control of the base is maintained with respect to the aryl boron reagent, and the correct boron ester is selected. Potassium tert-butoxide works well, but any excess of the base first inhibits and then poisons the catalyst. Lithium tert-butoxide performs very poorly, while even catalytic amounts of lithium additives also poison the catalyst. Meanwhile, a neopentane diol-based boron ester is required for best performance. As well as delivering this sought-after transformation, we have undertaken detailed mechanistic and computational investigations to probe the possible mechanism of the reaction and help explain the unexpected experimental observations.
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