Palladium-catalysed oxidative nucleophilic allylation between alkenes and activated ketimines. Issue 19 (9th August 2021)

• Record Type: Journal Article
• Authors: Li, Yue; Chen, Peng; Chen, Zhi-Chao; Du, Wei; Ouyang, Qin; Chen, Ying-Chun
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 19(2021)
• Page Start: 5418
• Page End: 5423
• Publication Date: 2021-08-09
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00505g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A direct linear regioselective oxidative allylation reaction between alkenes and activated ketimines has been developed by using a Pd(OAc)2 /2, 6-dimethyl-1, 4-benzoquinone system. Abstract : While electrophilic allylation with alkenes under oxidative palladium catalysis has been well explored, its umpolung nucleophilic allylation version under identical conditions has not been disclosed. Here we report that the direct and linear regioselective allylation reaction between alkenes and activated ketimines can be realised by using the classical Pd(OAc)2 /2, 6-dimethyl-1, 4-benzoquinone (2, 6-DMBQ) system, probably via the isomerisation of η 3 -π-allylpalladium complexes to η 1 -allylpalladium species in the absence of additional nucleophilic reagents. Diverse control and deuterium experiments have been conducted to elucidate the catalytic mechanism.