Synthesis and reactivity of 1,1-diborylalkanes towards C-C bond formation and related mechanisms

Identifier:  imarina:5132814

Handle: https://hdl.handle.net/20.500.11797/imarina5132814

Authors:  Miralles, N; Maza, RJ; Fernández, E

Abstract:
gem‐Diborylalkanes have emerged as efficient reagents for synthesizing organoboron compounds through selective C−C bond‐forming reactions. Activation of the 1,1‐diborylalkanes generates carbanions with enhanced stability that are able to react with a series of electrophiles, carbonyl compounds, imines and epoxides to promote formation of a new C−C bond. These new sets of reactions have become general for a wide range of substrates and they can be understood by alternative mechanisms that justify the potential use of these reagents. The formation of C-C(B) bonds can be achieved with chemo‐, diastereo‐ and enantioselectivity, because the nucleophilc α‐boryl or α‐diboryl carbanions attack in a stereoselective manner, by means of the catalyst involved. The synthesis of gem‐diborylalkanes has also been promoted by innovative methods and facilitates access to multiborylated reagents with different substituents and properties.