Highly Stereoselective Synthesis of 1,3‐Dienes through an Aryl to Vinyl 1,4‐Palladium Migration/Heck Sequence

• Published in: Angewandte Chemie International Edition Vol. 57; no. 20; pp. 5871 - 5875
• Main Authors: Hu, Tian‐Jiao, Li, Meng‐Yao, Zhao, Qian, Feng, Chen‐Guo, Lin, Guo‐Qiang
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 14-05-2018
• Edition: International ed. in English
• Subjects: alkenylation; Aromatic compounds; cross-coupling; C−H functionalization; Dienes; metal migration; Migration; Palladium; Stereoselectivity; Synthesis; C−H functionalization; alkenylation; cross-coupling; palladium; metal migration
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201801963

An efficient aryl to vinyl 1,4‐palladium migration/Heck sequence was developed for the stereoselective synthesis of 1,3‐dienes. High stereoselectivity was observed not only for 1,3‐dienes bearing two similar aryl groups at terminal positions, but also for those with configurations shown to be unfavorable with previous methods.
1,4 all: An efficient aryl to vinyl 1,4‐palladium/Heck sequence has been developed for the stereoselective synthesis of 1,3‐dienes. High stereoselectivity was observed not only for 1,3‐dienes bearing two similar aryl groups at terminal positions, but also for those with configurations shown to be unfavorable with previous methods.