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Pinacolborane

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The reduction of ketones with pinacolborane is catalyzed by NaOt-Bu at ambient temperature. The reaction is high yielding and general, providing complete conversion of aryl and dialkyl ketones. The active hydride source is the trialkoxyborohydride, which is believed to be present in low concentration under the reaction conditions.
I. P. Query, P. A. Squier, E. M. Larson, N. A. Isley, T. B. Clark, J. Org. Chem., 2011, 76, 6452-6456.


Homoleptic cyclopentadienyl lanthanide complexes are excellent catalysts for the hydroboration of various aldehydes and ketones with pinacolborane. These robust lanthanide catalysts exhibited high reactivity with low catalyst loadings under mild conditions, good functional group tolerability, and unique carbonyl-selectivity.
S. Chen, D. Yan, M. Xue, Y. Hong, Y. Yao, Q. Shen, Org. Lett., 2017, 19, 3382-3385.


An operationally convenient hydroboration of aldehydes and ketones employing Fe(acac)3 as precatalyst proceeded efficiently at room temperature to yield, after work up, 1 and 2 alcohols. A σ-bond metathesis mechanism with an Fe-H intermediate as key reactive species is postulated.
S. R. Tamang, M. Findlater, J. Org. Chem., 2017, 82, 12857-12862.


A simple [Ru(p-cymene)Cl2]2 complex is used as a catalyst precursor in a catalyzed hydroboration of nitriles and imines using pinacolborane with unprecedented catalytic efficiency.
A. Kaithal, B. Chatterjee, C. Gunanathan, J. Org. Chem., 2016, 81, 11153-11161.


1,2,4,3-triazaphospholenes halides catalyze the 1,2 hydroboration of imines and α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate.
C.-H. Tien, M. R. Adams, M. J. Ferguson, E. R. Johnson, A. W. H. Speed, Org. Lett., 2017, 19, 5565-5568.


A simple [Ru(p-cymene)Cl2]2 complex is used as a catalyst precursor in a catalyzed hydroboration of nitriles and imines using pinacolborane with unprecedented catalytic efficiency.
A. Kaithal, B. Chatterjee, C. Gunanathan, J. Org. Chem., 2016, 81, 11153-11161.