Abstract
Although there exists a variety of different catalysts for hydroboration of organic substrates such as aldehydes, ketones, imines, nitriles etc., recent evidence suggests that tetra-coordinate borohydride species, formed by activation, redistribution, or decomposition of boron reagents, are the true hydride donors. We then proposed that Me2S-BH3 could also act as a hydride donor for the reduction of various imines, as similar compounds have been observed to reduce carbonyl substrates. This boron reagent was shown to be an effective and chemoselective hydroboration reagent for a wide variety of imines.
Highlights
[1,2,3].Pinacolborane or catecholborane (HBcat) has been dominantly usedused as the hydroborating agent in these particular transformations, but the predominantly as the hydroborating agent in these particular transformations, but boron fragment (i.e., (i.e., Bcat/Bpin) was normally sacrificed to yield, for example, free alcothe boron fragment was normally sacrificed to yield, for example, free hols or amines. These reduction realcohols or amines. These reduction actions were mainly performed in the presence of catalytic amounts of a diverse range of reactions were mainly performed in the presence of catalytic amounts of a diverse rangeorganic/organometallic compounds
Several of the described hydroboration actions were efficient as catalyst loadings as low as 0.001 mol%, resulting in excellent subreactions were efficient as catalyst loadings as low as 0.001 mol%, resulting in excellent strate conversions
Instead of generating an “optimized” reaction condition with one of the examined imines and implementing this procedure for the rest of the substrates, we decided to optimize each transformation in order to maximize the substrate conversions
Summary
Hydroboration can can be be considered considered as as one one of of the the most most powerful powerful methods methods for for reduction reduction of various organic substrates such as aldehydes, ketones, imines, and nitriles of various organic substrates such as aldehydes, ketones, imines, and nitriles under under mild mild reaction (HBpin) or catecholborane (HBcat) has been prereaction conditions conditions[1,2,3]. Pinacolborane has been dominantly usedused as the hydroborating agent in these particular transformations, but the predominantly as the hydroborating agent in these particular transformations, but boron fragment (i.e., (i.e., Bcat/Bpin) was normally sacrificed to yield, for example, free alcothe boron fragment was normally sacrificed to yield, for example, free hols (from carbonyls) or amines (from imines/nitriles) These reduction actions were mainly performed in the presence of catalytic amounts of a diverse range of reactions were mainly performed in the presence of catalytic amounts of a diverse range (in)organic/organometallic compounds [4,5,6,7,8,9]. We disclose chemoselective hydroboration of imines using solely Me2 S-BH3 as the reducing agent in the absence of any activators and/or a protic solvent medium
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