839-96-3Relevant academic research and scientific papers
BH3 ? Me2S: An Alternative Hydride Source for NiH-Catalyzed Reductive Migratory Hydroarylation and Hydroalkenylation of Alkenes
Liu, Jiandong,Gong, Hegui,Zhu, Shaolin
supporting information, p. 1543 - 1546 (2021/03/03)
Borane dimethylsulfide (BMS) was found to be an efficient hydride source for nickel-hydride catalyzed reductive migratory hydrofunctionalization reactions. Catalytic reductive migratory hydroarylation and migratory hydroalkenylation were achieved with BMS in high yields and with excellent regioselectivity. A large-scale experiment employing as little as 0.5 equivalents of BH3 ? Me2S as the hydride source delivered the desired migratory hydroarylation product in high yield and selectivity.
Rapid Access to Highly Functionalized Alkyl Boronates by NiH-Catalyzed Remote Hydroarylation of Boron-Containing Alkenes
Zhang, Yao,Han, Bo,Zhu, Shaolin
, p. 13860 - 13864 (2019/08/08)
The direct and selective functionalization of relatively simple and readily accessible precursors to produce highly functionalized alkyl boronates is a synthetically useful process. Herein we report a NiH-catalyzed remote hydroarylation process that can, through a synergistic combination of chain walking and subsequent cross-coupling, introduce an aryl group at the adjacent carbon atom of alkyl boronates under mild conditions. By means of a preliminary experiment with moderate enantioselectivity, it was shown that an asymmetric version could also be realized.
Iridium-catalyzed borylation of secondary benzylic C-H bonds directed by a hydrosilane
Cho, Seung Hwan,Hartwig, John F.
, p. 8157 - 8160 (2013/07/05)
Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1, 10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.
