Abstract
Organoboron compounds play an irreplaceable role in synthetic chemistry and the related transformations based on the unique reactivity of C–B bond are potentially the most efficient methods for the synthesis of organic molecules. The synthetic importance of multiboron compounds in C–C bond formation and function transformation reactions is growing and the related borations of activated or nonactivated alkenes have been developed recently. However, introducing directly two boron moieties into the terminal sites of alkenes giving 1,1-diborylalkanes in a catalytic fashion has not been explored yet. Here we describe a synthetic strategy of 1,1-diborylalkanes via a Ni-catalyzed 1,1-diboration of readily available terminal alkenes. This methodology shows high level of chemoselectivity and regioselectivity and can be used to convert a large variety of terminal alkenes, such as vinylarenes, aliphatic alkenes and lower alkenes, to 1,1-diborylalkanes.
Highlights
Organoboron compounds play an irreplaceable role in synthetic chemistry and the related transformations based on the unique reactivity of C–B bond are potentially the most efficient methods for the synthesis of organic molecules
Because these compounds are usually air and moisture stable and easy to handle compared with Grignard reagents, organolithium reagents, and enable further transformations based on the unique reactivity of the C–B bond[6]
They can either be manipulated in enantioselective catalytic fashion[11,12,13,14,15] (Fig. 1b) and or they can provide powerful synthetic module for concise synthesis of complex molecules through multiple C–C bond formation[16,17,18,19,20,21,22] (Fig. 1c), function transformation reactions (Fig. 1d), or both
Summary
Organoboron compounds play an irreplaceable role in synthetic chemistry and the related transformations based on the unique reactivity of C–B bond are potentially the most efficient methods for the synthesis of organic molecules. Organoboron compounds are recognized as versatile building blocks and fundamental intermediates in organic synthesis[1,2,3,4,5] Because these compounds are usually air and moisture stable and easy to handle compared with Grignard reagents, organolithium reagents, and enable further transformations based on the unique reactivity of the C–B bond[6]. As an important class of organoboron compounds, it is undeniable that the 1,1-diborylalkanes show significant applications in organic synthesis They can either be manipulated in enantioselective catalytic fashion[11,12,13,14,15] (Fig. 1b) and or they can provide powerful synthetic module for concise synthesis of complex molecules through multiple C–C bond formation[16,17,18,19,20,21,22] (Fig. 1c), function transformation reactions (Fig. 1d), or both. Both synthesis of 1,1-diborylalkanes in synthetic chemistry and applications of alkenes from petrochemical industry will be greatly improved
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