环丙烷化
化学
试剂
光化学
氧化还原
烷基
三氟甲基
双功能
卤化物
组合化学
有机化学
催化作用
作者
James P. Phelan,Simon B. Lang,Jordan S. Compton,Christopher B. Kelly,Ryan Dykstra,Osvaldo Gutiérrez,Gary A. Molander
摘要
A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.
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