1310048-96-4Relevant academic research and scientific papers
Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones
Huang, Chia-Yu,Li, Chao-Jun,Li, Jianbin,Qiu, Zihang,Wang, Haining
, p. 13011 - 13020 (2020/09/01)
Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same deoxygenation manifold with aliphatic aldehydes and ketones, we also enable a concise synthesis of 1,1,2-tris(boronates), a family of compounds that currently lack efficient synthetic methods. Given its simplicity and versatility, we expect that this novel borylation approach could show great promise in organoboron synthesis and inspire more carbonyl deoxygenative transformations in both academic and industrial settings.
Synthesis of Benzyl-, Allyl-, and Allenyl-boronates via Copper-Catalyzed Borylation of Alcohols
Mao, Lujia,Szabó, Kálmán J.,Marder, Todd B.
supporting information, p. 1204 - 1207 (2017/03/14)
Alcohols are among the most abundant and readily available organic feedstocks in industrial processes. The direct catalytic functionalization of sp3 C-O bonds of alcohols remains the main challenge in this field. Here, we report a copper-cataly
Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage
Hu, Jiefeng,Sun, Heqing,Cai, Wangshui,Pu, Xinghui,Zhang, Yemin,Shi, Zhuangzhi
, p. 14 - 24 (2016/01/15)
By developing a mild Ni-catalyzed system, a method for direct borylation of sp2 and sp3 C-N bonds has been established. The key to this hightly efficient C-N bond borylative cleavage depends on the appropriate choice of the nickel catalyst Ni(COD)2, ICy·HCl as a ligand, and the use of 2-ethoxyethanol as the cosolvent. This transformation shows good functional group compatibility and can serve as a powerful synthetic tool for gram-scale synthesis and late-stage C-N borylation of complex compounds.
Transition-metal-free synthesis of pinacol alkylboronates from tosylhydrazones
Li, Huan,Wang, Long,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 2943 - 2946 (2012/04/18)
Highly efficient: Pinacol alkylboronates were synthesized by the reaction of tosylhydrazones with bis(pinacolato)diboron or pinacolborane under transition-metal-free conditions. This reaction represents an expeditious conversion of carbonyl functionality into a boronate group. Copyright
Chemoselective Suzuki coupling of diborylmethane for facile synthesis of benzylboronates
Endo, Kohei,Ohkubo, Takahiro,Shibata, Takanori
supporting information; experimental part, p. 3368 - 3371 (2011/09/12)
The chemoselective Pd-catalyzed Suzuki-Miyaura cross-coupling reaction using a diborylmethane is reported. The use of an equimolar amount of base with a diborylmethane realized chemoselective coupling for the synthesis of various benzylboronate derivatives. Sterically hindered aryl bromides can give products in moderate to excellent yields.
