n‐Butyllithium (1 mol %)‐catalyzed Hydroboration of Aldehydes and Ketones with Pinacolborane

Abstract

A practical and efficient protocol for the hydroboration of aldehydes and ketones using a pinacolborane and alkyl lithium system is demonstrated. A systematic evaluation showed that 1 mol % n-butyllithium afforded catalyzed hydroboration of aldehydes and ketones in a short reaction time under ambient conditions. Excellent yield, functional group tolerance, short reaction time, low catalyst loading, and gram-scale synthesis are the salient features of the proposed protocol.

n‐Butyllithium Catalyzed Hydroboration of Nitriles and Carbodiimides

“…However, a very high chemoselectivity of imine over nitrile reduction was observed. The result of these competitive experiments were consistent ones reported using THF as solvent [13] …”

Asymmetric ketone hydroboration catalyzed by alkali metal complexes derived from BINOL ligands

“…As a result, the utilization of simple, commercially available group I metal salts has been at the forefront of this research area. Several groups have recently made major advancements demonstrating that simple sodium salts (NaO t Bu, NaH and NaOH) [8][9][10] and lithium salts ( n BuLi and LiHBEt3) [11][12][13] are highly active catalysts for carbonyl reductions. The simplicity of these alkali metal species suggests that they could serve as ideal precatalysts for the development of enantioselective s-block catalyzed ketone reductions in the presence of a chiral ligand.…”

Hydrosilylation and hydroboration in a sustainable manner: from Earth-abundant catalysts to catalyst-free solutions

“…Concurrently, the Bao and An groups reported that the readily accessible n-butyllithium reagent is an extremely active catalyst for the hydroboration of a variety of aldehydes and ketones (Scheme 15). 118,119 The low catalyst loading is remarkable (even to 0.1 mol%, under solvent-free conditions). However, it should be noted that commercially available n BuLi is always marketed as a solution in alkanes.…”