化学
位阻效应
钯
赫克反应
部分
组合化学
催化作用
卤化物
有机化学
作者
Bowen Li,Bangke Luo,He Yang,Wenjun Tang
标识
DOI:10.1002/ange.202209087
摘要
Abstract The Heck reaction between N ‐heteroaryl halides and heterocyclic alkenes provides a convenient approach to biologically relevant α‐heteroaryl functionalized heterocycles, yet reactions of this type have been challenging due to strong N ‐heteroaryl coordination to palladium metal, which causes catalyst poisoning. In this report, an efficient palladium‐catalyzed Heck reaction between N ‐heteroaryl halides and heterocyclic olefins is established, leading to a variety of α‐heteroaryl substituted heterocycles. The method features an unprecedented broad substrate scope and excellent functional group compatibility. The employment of a sterically bulky P, P=O ligand containing an anthryl moiety is crucial for this transformation due to the coordinative unsaturation facilitated by its steric bulkiness. The asymmetric variant of the Heck reaction is achieved with ( S )‐DTBM‐SEGPHOS via a cationic palladium pathway, which has enabled an efficient asymmetric synthesis of ( S )‐nicotine and its analogues.
科研通智能强力驱动
Strongly Powered by AbleSci AI