83947-57-3Relevant articles and documents
Selective Benzylic CH-Borylations by Tandem Cobalt Catalysis
Bauer, Matthias,Ghosh, Pradip,Jacobi von Wangelin, Axel,Schoch, Roland
supporting information, (2021/11/27)
Metal-catalyzed C?H activations are environmentally and economically attractive synthetic strategies for the construction of functional molecules as they obviate the need for pre-functionalized substrates and minimize waste generation. Great challenges reside in the control of selectivities, the utilization of unbiased hydrocarbons, and the operation of atom-economical dehydrocoupling mechanisms. An especially mild borylation of benzylic CH bonds was developed with the ligand-free pre-catalyst Co[N(SiMe3)2]2 and the bench-stable and inexpensive borylation reagent B2pin2 that produces H2 as the only by-product. A full set of kinetic, spectroscopic, and preparative mechanistic studies are indicative of a tandem catalysis mechanism of CH-borylation and dehydrocoupling via molecular CoI catalysts.
Metal-free synthesis of gem -silylboronate esters and their Pd(0)-catalyzed cross-coupling with aryliodides
Wu, Chaoqiang,Bao, Zhicheng,Xu, Xing,Wang, Jianbo
, p. 5714 - 5724 (2019/06/18)
A transition-metal-free method for the synthesis of gem-silylboronate esters with arylboronic acids and trimethylsilyldiazomethane (TMSCHN2) has been developed. This transformation is a straightforward homologation of arylboronic acids and features wide substrate scope and good functional-group tolerance. The gem-silylboronate esters undergo efficient Suzuki-Miyaura cross-coupling with aryliodides and the silyl group of the product can be further functionalized. Tertiary carbon centers with different substituents can be constructed successfully by selective and sequential functionalization.
Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids
Bomio, Claudio,Kabeshov, Mikhail A.,Lit, Arthur R.,Lau, Shing-Hing,Ehlert, Janna,Battilocchio, Claudio,Ley, Steven V.
, p. 6071 - 6075 (2017/08/29)
By means of computational and experimental mechanistic studies the fundamental role of boroxines in the reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metal-free carbon-carbon homologation of aryl and vinyl boroxines using TMSCHN2, giving access to TMS-pinacol boronic ester products, was developed.
