1286795-63-8Relevant academic research and scientific papers
Directing-Group-Based Strategy Enabling Intermolecular Heck-Type Reaction of Cycloketone Oxime Esters and Unactivated Alkenes
Cheng, Gui-Juan,Deng, Yi,Fu, Junkai,Li, Xuexiang,Wang, Hongwei,Zhao, Chunyang,Zhou, Yu
, p. 3524 - 3530 (2020)
A new type of coupling between unactivated olefins and nonstabilized alkyl radicals was achieved, which enabled the first intermolecular Heck-type reaction of cycloketone oxime esters and unactivated alkenes. This directing-group-based strategy was compatible with various unactivated alkenes and cyclobutanone-, cyclopentanone-, and cyclohexanone-derived oxime esters. Density functional theory calculations showed that both excellent regioselectivities and good diastereoselectivities could be ascribed to the 2-butanol-assisted concerted H-OBz elimination of the conformationally strained metallacyclic transition state.
Directed Cobalt-Catalyzed anti-Markovnikov Hydroalkylation of Unactivated Alkenes Enabled by "co-H" Catalysis
Yang, Dandan,Huang, Hai,Li, Meng-Hui,Si, Xiao-Ju,Zhang, He,Niu, Jun-Long,Song, Mao-Ping
, p. 4333 - 4338 (2020/06/04)
The earth-abundant cobalt-catalyzed anti-Markovnikov hydroalkylation of unactivated alkenes with oxime esters was achieved by introducing an 8-aminoquinoline directing group on the alkenes. The catalytic system, consisting of commercially available Co(acac)3 and PhMeSiH2, enables the construction of unfunctionalized C(sp3)-C(sp3) bonds and features exclusive anti-Markovnikov selectivity, good functional group tolerance, and the avoidance of an extra ligand, oxidant, or base. Mechanistic insight into this new catalytic system indicates the involvement of both alkyl radical and cobalt hydride intermediates.
