环丁烷
螺旋桨烷
双环分子
催化作用
化学
铜
有机化学
计算化学
环加成
作者
Xiao-Tian Feng,Qiao‐Qiao Min,Xiangfeng Zeng,Hang Zhao,Xingang Zhang
标识
DOI:10.1021/acscatal.4c00281
摘要
A controllable strategy using [1.1.1]propellane (TCP) for the selective synthesis of gem-difluoroallylated bicyclo[1.1.1]pentanes (BCPs) and cyclobutanes (CyBus) with electrophilic fluoroalkylating reagents, 3,3-difluoroallyl sulfonium salts (DFASs), and organometallic reagents, including Grignard and organozinc reagents, has been developed. In this strategy, a stepwise procedure by nucleophilic addition of organometallic reagents to TCP, followed by copper-catalyzed cross-coupling with DFASs, favors the formation of fluoroalkylated BCPs. A one-pot copper-catalyzed three-component carbene transfer reaction of organozinc reagents and DFASs with TCP as the precursor prefers the generation of fluorinated CyBus, featuring the formation of two C–C bonds and a quaternary carbon center. This innovative carbene transfer reaction also leads to a unique and unexpected BCP and CyBu-connected structure. Applying these approaches leads to the diversified synthesis of complex fluorinated strained rings, rendering this strategy attractive for applications in medicinal chemistry.
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