The radical-involved 1,2-difunctionalization of alkenes has developed into a robust tool for preparation of complex organic molecules. Despite significant advances in this area, the catalytic asymmetric version still remains a challenging task mainly due to the difficulty in the stereocontrol of the highly reactive radical intermediates. Recently, owing to the good single-electron transfer ability and coordination with chiral ligands of copper catalysts, remarkable achievements in radical-involved asymmetric alkene difunctionalization have been made via synergistic combination of copper and chiral ligands. This tutorial review highlights the recent progress in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes and the mechanistic scenarios governing the stereocontrol, with an emphasis on utilization of chiral ligands.

Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes

Nickel-catalyzed reductive cross-coupling reactions have emerged as powerful methods to join two electrophiles These reactions have proven particularly useful for the coupling of sec-alkyl electrophiles to form stereogenic centers; however, the development of enantioselective variants remains challenging In this Perspective, we summarize the progress that has been made toward Ni-catalyzed enantioselective reductive cross-coupling reactions

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Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Advances in nickel-catalyzed cross-coupling reactions have expanded the chemical space of accessible structures and enabled new synthetic disconnections. The unique properties of Ni catalysts facilitate the activation of traditionally inert substrates, tolerate alkyl coupling partners that undergo decomposition via β-hydride (β-H) elimination with Pd, and enable stereoconvergent cross-couplings. The radical pathways accessed by Ni catalysts have been merged with photoredox and electrochemical catalysis to achieve new reactivity. The growing utility of Ni catalysis is, in no small part, due to advances in our fundamental understanding of the properties of Ni catalysts and the mechanisms by which the reactions occur. This review highlights recent important contributions to the field with an emphasis on studies that have afforded mechanistic insight.

Mechanisms of Nickel-Catalyzed Cross-Coupling Reactions

Nickel-catalyzed three-component alkene difunctionalization has rapidly emerged as a powerful tool for forging two C–C bonds in a single reaction. Building upon the powerful modes of bond construction in traditional two-component cross-coupling, various research groups have demonstrated the versatility of nickel in enabling catalytic 1,2-dicarbofunctionalization using a wide range of carbon-based electrophiles and nucleophiles and in a fully intermolecular fashion. Though this area has emerged only recently, the last few years have witnessed a proliferation of publications on this topic, underscoring the potential of this strategy to develop into a general platform that offers high regio- and stereoselectivity. This minireview highlights the recent progress in the area of intermolecular 1,2-dicarbofunctionalization of alkenes via nickel catalysis and discusses lingering challenges within this reactivity paradigm.

/pdf/recent-developments-in-nickel-catalyzed-intermolecular-4jpt38g1u2.pdf

Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes

1,2-Dicarbofunctionalization of alkenes has emerged as an efficient synthetic strategy for preparing substituted molecules by coupling readily available alkenes with electrophiles and/or nucleophiles Nickel complexes serve as effective catalysts owing to their tendency to undergo facile oxidative addition and slow β-hydride elimination, and their capability to access both two-electron and radical pathways Two-component alkene functionalization reactions have achieved high chemo-, regio-, and stereoselectivities by tethering one of the coupling partners to the alkene substrate Three-component reactions, however, often incorporate directing groups to control the selectivity Only a few examples of directing-group-free difunctionalizations of unactivated alkenes have been reported Therefore, great opportunities exist for the development of three-component difunctionalization reactions with broad substrate scopes and tunable chemo-, regio-, and stereoselectivities

Nickel-Catalyzed Dicarbofunctionalization of Alkenes

A Ni-catalyzed enantioselective reductive diarylation of activated alkenes by domino cyclizative/cross-coupling of two aryl bromides is developed. This reaction proceeds under very mild conditions and shows broad substrate scope, without requiring the use of preformed organometallic reagents. Moreover, this approach provides direct access to various bis-heterocycles bearing all-carbon quaternary centers in synthetically useful yields (up to 81%) with excellent enantioselectivity (>30 examples, 90–99% ee).

Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling.

Transition-metal-catalytic domino reactions represent important advances in synthetic organic chemistry. Their development benefits synthesis by providing highly efficient and step-economical metho...

Ni-Catalyzed Regio- and Enantioselective Domino ReductiveCyclization: One-Pot Synthesis of 2,3-Fused Cyclopentannulated Indolines

Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles.

Ni-Catalyzed Reductive Arylacylation of Alkenes toward Carbonyl-Containing Oxindoles

A Ni-catalyzed enantioselective reductive diarylation of alkenes through a tandem Heck cyclization/cross coupling of two structurally distinguished aryl bromides is accomplished for the first time. This reaction takes place under very mild conditions with high efficiency and tolerates a variety of functional groups. Thus, it provides a rapid access to various medicinally relevant bis-heterocycles containing all-carbon quaternary centers with very high enantioselectivity.

Enantioselective Reductive Diarylation of Alkenes by Ni-Catalyzed Domino Heck Cyclization/Cross Coupling

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