20396-66-1Relevant articles and documents
Selective electrocatalytic hydroboration of aryl alkenes
Zhang, Yahui,Zhao, Xiangyu,Bi, Ce,Lu, Wenqi,Song, Mengyuan,Wang, Dongdong,Qing, Guangyan
supporting information, p. 1691 - 1699 (2021/03/09)
Organoboron compounds are powerful precursors of value-added organic compounds in synthetic chemistry, and transition metal-catalysed borylation has always been dominant. To avoid toxic reagents and costs associated with metal catalysts, simpler, more eco
Elucidation of the Formation Mechanisms of the Octahydrotriborate Anion (B3H8-) through the Nucleophilicity of the B-H Bond
Chen, Xi-Meng,Ma, Nana,Zhang, Qian-Fan,Wang, Jin,Feng, Xiaoge,Wei, Changgeng,Wang, Lai-Sheng,Zhang, Jie,Chen, Xuenian
supporting information, p. 6718 - 6726 (2018/05/23)
Boron compounds are well-known electrophiles. Much less known are their nucleophilic properties. By recognition of the nucleophilicity of the B-H bond, the formation mechanism of octahydrotriborate (B3H8-) was elucidated on the bases of both experimental and computational investigations. Two possible routes from the reaction of BH4- and THF·BH3 to B3H8- were proposed, both involving the B2H6 and BH4- intermediates. The two pathways consist of a set of complicated intermediates, which can convert to each other reversibly at room temperature and can be represented by a reaction circle. Only under reflux can the B2H6 and BH4- intermediates be converted to B2H5- and BH3(H2) via a high energy barrier, from which H2 elimination occurs to yield the B3H8- final product. The formation of B2H6 from THF·BH3 by nucleophilic substitution of the B-H bond was captured and identified, and the reaction of B2H6 with BH4- to produce B3H8- was confirmed experimentally. On the bases of the formation mechanisms of B3H8-, we have developed a facile synthetic method for MB3H8 (M = Li and Na) in high yields by directly reacting the corresponding MBH4 salts with THF·BH3. In the new synthetic method for MB3H8, no electron carriers are needed, allowing convenient preparation of MB3H8 in large scales and paving the way for their wide applications.
Application of cooperative iron/copper catalysis to a palladium-free borylation of aryl bromides with pinacolborane
Labre, Flavien,Gimbert, Yves,Bannwarth, Pierre,Olivero, Sandra,Dunach, Elisabet,Chavant, Pierre Y.
supporting information, p. 2366 - 2369 (2014/05/20)
A new cooperative copper/iron catalysis for the borylation of various aryl bromides with pinacolborane, at -10 °C, is reported. Use of the toxic, precious metal Pd is avoided. The mechanism of the protodebromination side reaction is discussed.