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Synthesis and Reactivity of 1,1‐Diborylalkanes towards C–C Bond Formation and Related Mechanisms
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-01-31 , DOI: 10.1002/adsc.201701390
Núria Miralles 1 , Ricardo J. Maza 1 , Elena Fernández 1
Affiliation  

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.

中文翻译:

1,1-二硼烷基烷烃的合成及其对CC键形成的反应性及相关机理

宝石-二硼烷基烷烃已成为通过选择性C-C键形成反应合成有机硼化合物的有效试剂。1,1-二硼烷基烷烃的活化产生的碳负离子具有增强的稳定性,能够与一系列亲电试剂,羰基化合物,亚胺和环氧化物反应,从而促进新的C-C键的形成。这些新的反应组已广泛用于各种底物,并且可以通过证明这些试剂潜在用途合理的替代机制来理解。C–C(B)键的形成可以通过化学,非对映体和对映体选择性实现,因为亲核体的α-硼烷基或α-二硼烷基碳负离子会通过所涉及的催化剂以立体选择性方式发生攻击。宝石的合成二硼烷基烷烃也已通过创新方法得到推广,并促进了具有不同取代基和性质的多硼化试剂的获取。
更新日期:2018-01-31
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