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Triple cross-electrophile coupling enabled by palladium/norbornene cooperative catalysis

发布时间：2026-06-21
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DOI码：10.1126/sciadv.adu4573
发表刊物：Science Advances
摘要：Cross-electrophile coupling (XEC) is a powerful strategy for forming C–C bonds in synthetic organic chemistry. While XEC reactions between two electrophiles are well established, those involving three distinct electrophiles have remained underdeveloped. Herein, we report an intriguing formal triple XEC enabled by palladium/norbornene cooperative catalysis. Readily available aryl iodides, alkyl/aryl bromides, and propargyl esters are used as the distinct electrophilic coupling partners, leading to the synthesis of a diverse array of tetrasubstituted allenes. In particular, the challenging asymmetric formal triple XEC has also been realized through palladium/chiral norbornene cooperative catalysis, which uses the sterically hindered 2,6-disubstituted aryl bromides as the arylating reagents to prepare tetrasubstituted allenes bearing an axially chiral biaryl unit. Density functional theory calculations reveal that the selection of propargyl esters as electrophilic terminating reagents is key to the success of this reaction because it enables a thermodynamically favored pathway for reaction termination involving alkyne insertion followed by β-O elimination.
学科门类：理学
卷号：11
期号：18
页面范围：eadu4573
ISSN号：2375-2548
是否译文：否
发表时间：2025-04-30
收录刊物：SCI
发布期刊链接：https://www.science.org/doi/10.1126/sciadv.adu4573