Enhanced Efficiency of Amide-Substituted Quinuclidine-Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins  

作　　者：Xiao Yang Mengdi Ma Meichen Xu Yubing Pang Haiying Zhao Juntao Ye 

机构地区：[1]Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules,College of Chemistry and Chemical Engineering,Inner Mongolia University,Hohhot,Inner Mongolia 010021,China [2]Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs,School of Chemistry and Chemical Engineering,Shanghai Jiao Tong University,Shanghai 200240,China

出　　处：《Chinese Journal of Chemistry》2024年第24期3227-3233,共7页中国化学(英文版)

基　　金：the National Natural Science Foundation of China(grant nos.22371180 and 22001163 to Y.J.and 22361032 to H.Z.);Shanghai Jiao Tong University(SJTU)is acknowledged.Dr.Pandaram Sakthivel(SJTU)is acknowledged for reproducing the results of compounds 6,10,and 21.

摘　　要：An amide-substituted quinuclidine-borane has been identified as a more efficient hydridic hydrogen atom transfer(HAT)catalyst for the hydroalkylation of unactivated olefins under visible-light irradiation.^(1)H NMR titration experiments reveal that the amide moiety of the quinuclidine-borane catalyst forms stronger hydrogen bonds with the carbonyl substrates,thereby improving the reaction yields.Furthermore,it was found that the reaction yields correlate well with the association constant between the quinuclidine-borane catalyst and the carbonyl substrate.A scale-up reaction using a continuous-flow photoreactor has also been demonstrated.

关 键 词：Hydrogen atom transfer BORANE Unactivated olefin HYDROALKYLATION Photocatalysis 

分 类 号：O62[理学—有机化学]