化学
环加成
双环分子
催化作用
吡啶
产量(工程)
催化循环
自由基环化
立体化学
组合化学
药物化学
有机化学
材料科学
冶金
作者
Tao Yu,Jinbo Yang,Zhijun Wang,Zhengwei Ding,Min Xu,Jingru Wen,Liang Xu,Pengfei Li
摘要
In contrast to the traditional and widely-used cycloaddition reactions involving at least a π bond component, a [2σ + 2σ] radical cycloaddition between bicyclo[1.1.0]butanes (BCBs) and cyclopropyl ketones has been developed to provide a modular, concise, and atom-economical synthetic route to substituted bicyclo[3.1.1]heptane (BCH) derivatives that are 3D bioisosteres of benzenes and core skeleton of a number of terpene natural products. The reaction was catalyzed by a combination of simple tetraalkoxydiboron(4) compound B2pin2 and 3-pentyl isonicotinate. The broad substrate scope has been demonstrated by synthesizing a series of new highly functionalized BCHs with up to six substituents on the core with up to 99% isolated yield. Computational mechanistic investigations supported a pyridine-assisted boronyl radical catalytic cycle.
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