Recent Progress in Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes
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Abstract
As readily available and abundant industrial feedstocks, alkenes have emerged as versatile platform for constructing value-added targets. Transition metal-catalyzed dicarbofunctionalizations reactions forge two carbon-carbon bonds in one step with construction of two vicinal saturated carbon centers, providing profound synthetic potential in organic synthesis and pharmaceutical chemistry. In particular, nickel-catalyzed reductive dicarbofunctionalization of alkenes has witnessed remarkable progress in recent years. Compared to conventional redox-neutral dicarbofunctionalization strategy, reductive variant offers significant advantages, such as no use of pre-formed organometallic reagents, operational simplicity and mild reaction conditions. This review summarizes developments of nickel-catalyzed reductive dicarbofunctionalization of alkenes to forge diverse carbon-carbon bonds in the absence of stoichiometric carbon nucleophiles. The mechanistic considerations are comprehensively discussed, including two-electron migratory insertion and the single-electron radical addition pathways. Furthermore, we provide critical insights into future directions and potential challenges in this area, highlighting opportunities for further methodology development and applications for nickel-catalyzed reductive dicarbofunctionalization of alkenes.
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Abstract
As readily available and abundant industrial feedstocks, alkenes have emerged as versatile platform for constructing value-added targets. Transition metal-catalyzed dicarbofunctionalizations reactions forge two carbon-carbon bonds in one step with construction of two vicinal saturated carbon centers, providing profound synthetic potential in organic synthesis and pharmaceutical chemistry. In particular, nickel-catalyzed reductive dicarbofunctionalization of alkenes has witnessed remarkable progress in recent years. Compared to conventional redox-neutral dicarbofunctionalization strategy, reductive variant offers significant advantages, such as no use of pre-formed organometallic reagents, operational simplicity and mild reaction conditions. This review summarizes developments of nickel-catalyzed reductive dicarbofunctionalization of alkenes to forge diverse carbon-carbon bonds in the absence of stoichiometric carbon nucleophiles. The mechanistic considerations are comprehensively discussed, including two-electron migratory insertion and the single-electron radical addition pathways. Furthermore, we provide critical insights into future directions and potential challenges in this area, highlighting opportunities for further methodology development and applications for nickel-catalyzed reductive dicarbofunctionalization of alkenes.
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Chinese Journal of Chemistry
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Yucheng Liu, Fu-Yu Li, Muneer-ul-Shafi Bhat, et al.
Recent Progress in Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes. Authorea. 04 July 2025.
DOI: https://doi.org/10.22541/au.175161451.14156353/v1
DOI: https://doi.org/10.22541/au.175161451.14156353/v1
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