化学
位阻效应
卡宾
催化作用
配体(生物化学)
还原消去
组合化学
炔烃
偶联反应
分子
过渡金属
磷化氢
光化学
立体化学
有机化学
受体
生物化学
作者
Ming-Chun Wu,Yu‐Fu Liang,Titel Jurca,Glenn P. A. Yap,T. C. Leung,Tiow‐Gan Ong
摘要
Dicarbon is a reactive carbon allotrope that naturally exists only in the high-temperature medium of stellar space. We report the successful preparation of a series of bottleable phosphine-stabilized dicarbon (PDC) molecules. We explore the use of these molecules as a new complementary class of carbene-like ligands featuring strong σ-donor (>NHCs and CAAcs) but weak π-acceptor properties. Steric map analysis of PDC based on Cavallo’s SambVca program reveals comparable steric volume bulk of 32.5%, similar to the conventional IMes carbene. However, our PDCs exhibit dynamic steric flexibility modulated by the nature of the metal complexes and catalytic reaction environment. We demonstrate the catalytic utility of the PDC framework by its successful implementation for Suzuki–Miyaura cross-coupling and the reductive coupling reaction of an aldehyde and alkyne. Detailed investigations of the reductive coupling reaction reveal an important secondary interaction between PDC and metal complexes, which plays a critical role in the catalytic system.
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