2020
DOI: 10.1002/cjoc.202000224
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Nickel‐CatalyzedDicarbofunctionalization of Alkenes

Abstract: As a straightforward strategy for rapidly increasing molecular complexity, dicarbofunctionalization of alkenes has attracted substantial interests of organic synthesis, medicine chemistry, and materials science. Nickel-catalyzed cascade dicarbofunctionalizations have been flourished in this area recently, and nickel-mediated radical pathways particularly offer new opportunities in conjunctive cross-couplings with alkyl coupling partners. Herein, we give a comprehensive review of nickel-catalyzed dicarbofunctio… Show more

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Cited by 185 publications
(40 citation statements)
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References 167 publications
(179 reference statements)
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“…In the last decade, transition-metal catalyzed enantioselective dicarbofunctionalizations of tethered alkenes has evolved into a reliable method to construct the scaffold of chiral benzene-fused cyclic compounds. [1][2][3][4][5][6] The majority of these reactions relies on a facially selective Heck-type arylmetallation of the pendant olefinic unit as the enantiodetermining step, 7 which is followed by trapping of the generated σ-alkylmetal species with either a nucleophile or an electrophile. Based on this strategy, asymmetric aryl-alkylation, [8][9][10] diarylation, [10][11][12][13] arylbenzylation, 14 aryl-alkenylation 15,16 and aryl-alkynylation 13,17,18 of incorporated alkenes have been developed under palladium, copper or nickel catalysis.…”
Section: Introductionmentioning
confidence: 99%
“…In the last decade, transition-metal catalyzed enantioselective dicarbofunctionalizations of tethered alkenes has evolved into a reliable method to construct the scaffold of chiral benzene-fused cyclic compounds. [1][2][3][4][5][6] The majority of these reactions relies on a facially selective Heck-type arylmetallation of the pendant olefinic unit as the enantiodetermining step, 7 which is followed by trapping of the generated σ-alkylmetal species with either a nucleophile or an electrophile. Based on this strategy, asymmetric aryl-alkylation, [8][9][10] diarylation, [10][11][12][13] arylbenzylation, 14 aryl-alkenylation 15,16 and aryl-alkynylation 13,17,18 of incorporated alkenes have been developed under palladium, copper or nickel catalysis.…”
Section: Introductionmentioning
confidence: 99%
“…Alkenes are arguably one of the most privileged and versatile chemicals in organic synthesis because a diverse range of functional groups could be readily introduced across the C = C π system by many classic vicinal difunctionalization reactions 1 4 . In this context, one of the most investigated and fundamental transformations is the intermolecular three-component alkene vicinal dicarbofunctionalization (DCF) reaction, which allows installation of two different carbon fragments.…”
Section: Introductionmentioning
confidence: 99%
“…Subsequent 1,2-migratory insertion followed by a sequential electrophilic amination reaction will yield the arylamination product. [34][35][36][37][38][39] Critical to the success of this process, the reaction must be initiated by a transmetalation step to form the Ni-Ar species, which is rarely reported and challenging because of the fact that most of three-component difunctionalization reactions utilizing arylboron reagents were initiated by oxidative addition with electrophiles to Ni(0) catalyst, thus furnishing products that incorporate electrophile at the terminal position and aryl at the internal position. Herein, we reported a new approach for the 1,2-arylamination of unactivated alkenes under practical and easily handled Ni(II) catalytic system with commercial available arylboronic acids and readily prepared Obenzoylhydroxylamines with excellent regio-and diastereocontrol (Fig.…”
Section: Introductionmentioning
confidence: 99%