Bidentate auxiliary-directed alkenyl C–H allylation via exo-palladacycles: synthesis of branched 1, 4-dienes. Issue 90 (28th October 2019)

• Record Type: Journal Article
• Authors: Shen, Cong; Lu, Xiunan; Zhang, Jian; Ding, Liyuan; Sun, Yaling; Zhong, Guofu
• Is Part Of: Chemical communications. Volume 55:Issue 90(2019)
• Page Start: 13582
• Page End: 13585
• Publication Date: 2019-10-28
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc07466j
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An alkenyl C–H allylation by exo -palladacycle is demonstrated to produce branched skipped dienes, employing alkenyl amides and allyl carbonates. Abstract : An alkenyl C–H allylation by an exo -palladacycle intermediate is demonstrated, employing unactivated ( Z )-alkenes and allyl carbonates. With the use of an 8-aminoquinoline (AQ) derived amide as the directing group, the N, N -bidentate-chelation-assisted C–H activation protocol proceeded under mild and oxidant-free conditions with excellent selectivity. The utility of this approach is demonstrated by the preparative scale, selective conversion of inseparable Z / E alkenes and ready removal of the amide auxiliary to provide the corresponding ester.