Stereospecific Assembly of Trisubstituted Alkenes via Photoinduced Nitrogen-Centered Radical-Triggered C—C Bond Cleavage/Functionalization of Oxime Esters  

作　　者：Yu Bao Zhi-Jie Song Jin-Long Dai Shenghu Yan Yue Zhang Jia-Yin Wang Guigen Li 

机构地区：[1]School of Pharmacy,Changzhou University,Changzhou,Jiangsu 213164,China [2]Department of Chemistry and Biochemistry,Texas Tech University,79409,USA

出　　处：《Chinese Journal of Chemistry》2024年第12期1399-1406,共8页中国化学（英文版）

基　　金：the school level research projects of Changzhou University(No.ZMF23020007).

摘　　要：Comprehensive Summary A general and convenient photoredox-catalyzed acylation and alkylcyanation of MBH acetates has been established,enabling the assembly of the C(sp2)–C(sp3)bond by a nitrogen-centered radical strategy for the synthesis of trisubstituted alkenes in moderate to excellent chemical yields(48 examples in total).The reaction of MBH acetates with acyl(indanone)oxime esters afforded trisubstituted alkenes containing 1,4-dicarbonyl groups.Interestingly,the use of Eosin Y as a photocatalyst in the catalytic system resulted in the formation of distal cyano group-anchored trisubstituted alkenes via deconstructive functionalization of cycloketone oxime esters.Notably,these resulting 1,4-dicarbonyl compounds could be applied to late-stage transformations,providing important methods for the synthesis of dihydropyridazin-3(2H)-one.

关 键 词：Photocatalysis Radical reactions MBH acetates Oxime esters STEREOSELECTIVITY ACYLATION ALKYLATION Green chemistry 

分 类 号：O62[理学—有机化学]