烷基
无水的
卤化物
芳基
化学
硼酸
偶联反应
铃木反应
配体(生物化学)
联轴节(管道)
组合化学
药物化学
有机化学
催化作用
生物化学
受体
机械工程
工程类
作者
Martin Böck,Scott E. Denmark
标识
DOI:10.1021/acs.joc.4c00089
摘要
A rapid, anhydrous Suzuki-Miyaura cross-coupling of alkylboronic esters with aryl halides is described. Parallel experimentation revealed that the combination of AntPhos, an oxaphosphole ligand, neopentyldiol alkylboronic esters, and potassium trimethylsilanolate (TMSOK) enables successful cross-coupling. In general, reactions proceed in under 1 h with good yields and high linear/branched (l/b) selectivities. Crucially, two literature examples which previously took >20 h to reach completion were accomplished in a fraction of the time with the method described herein. Mechanistic studies revealed that the reaction proceeds through a stereoretentive pathway and identified the boronic ester skeleton as a predominant pathway for deleterious protodehalogenation.
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