1722-26-5Relevant articles and documents
Hydrodechlorination of Et3NBCl3 catalyzed by amorphous nickel boride - A mechanistic approach
Reller, Christian,Mertens, Florian O.R.L.
, p. 450 - 459 (2014)
The catalytic hydrodechlorination of BCl3 with molecular hydrogen in the presence of tertiary amines is a viable strategy for the energy-efficient generation of valuable B-H bonds. A mechanistic study based on experiments with isolated intermediates and deuterium labeling experiments is presented. The occurrence of the rate-limiting reverse reaction from the insoluble Et3NHCl adduct was identified as a major cause of low Et3NBH3 yields. In addition, amines with NCH2 units, which also serve in the corresponding cases as solvents, have a strong influence on the reaction kinetics; they are directly involved in the hydrogen transfer at elevated temperatures and assume the role of a cocatalyst. A catalytic cycle for the reaction on a nickel boride catalyst is proposed. Copyright
Amine-borane hydrolysis at bridgehead nitrogen
Kelly, Henry C.,Underwood III, Justin A.
, p. 1202 - 1204 (1969)
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The quest for silylhydroboranes: (Me3Si)3SiBH 2
Arp, Henning,Marschner, Christoph,Baumgartner, Judith
, p. 9270 - 9274 (2010)
Reaction of BH3.NEt3 with tris(trimethylsilyl) silylpotassium yielded the respective silylboranate. Abstraction of a hydride with B(C6F5)3 led to the neutral silylborane, which could be derivatised as an Et3N adduct. Treatment of the boranate with Cp2Ti(btmsa) resulted in exchange of THF coordinating to potassium by Cp2Ti(btmsa). The Royal Society of Chemistry.
Activation of sodium borohydride via carbonyl reduction for the synthesis of amine- And phosphine-boranes
Hamann, Henry J.,Lin, Randy,Veeraraghavan Ramachandran, P.
supporting information, p. 16770 - 16774 (2021/12/08)
A highly versatile synthesis of amine-boranes via carbonyl reduction by sodium borohydride is described. Unlike the prior bicarbonate-mediated protocol, which proceeds via a salt metathesis reaction, the carbon dioxide-mediated synthesis proceeds via reduction to a monoformatoborohydride intermediate. This has been verified by spectroscopic analysis, and by using aldehydes and ketones as the carbonyl source for the activation of sodium borohydride. This process has been used to produce borane complexes with 1°-, 2°-, and 3°-amines, including those with borane reactive functionalities, heteroarylamines, and a series of phosphines.
Photocatalytic C-F Bond Borylation of Polyfluoroarenes with NHC-boranes
Chen, Kai,Chen, Xiao-Qing,Hu, Yuan-Zhuo,Xia, Peng-Ju,Xiang, Hao-Yue,Xiao, Jun-An,Yang, Hua,Ye, Zhi-Peng
supporting information, p. 1742 - 1747 (2020/03/24)
The first photoredox-catalyzed defluoroborylation of polyfluoroarenes with NHC-BH3 has been facilely achieved at room temperature via a single-electron-transfer (SET)/radical addition pathway. This new strategy makes full use of the advantage of photoredox catalysis to generate the key boryl radical via direct activation of a B-H bond. Good functional group tolerance and high regioselectivity offer this protocol incomparable advantages in preparing a wide array of valuable polyfluoroarylboron compounds. Moreover, both computational and experimental studies were performed to illustrate the reaction mechanism.
The role of ammonia in promoting ammonia borane synthesis
Ramachandran, P. Veeraraghavan,Kulkarni, Ameya S.
, p. 16433 - 16440 (2016/10/31)
Ammonia promotes the synthesis of pure ammonia borane (AB) in excellent yields from sodium borohydride and ammonium sulfate in tetrahydrofuran under ambient conditions. An examination of the influence of added ammonia reveals that it is incorporated into the product AB, contrary to its perceived function as a catalyst or a co-solvent. Mechanistic studies point to a nucleophilic attack by ammonia on ammonium borohydride with concurrent dehydrogenation to yield AB.
