Development of Nickel-Catalyzed Cross-Coupling of Alcohol Derivatives to Construct Carbon-Carbon Bonds

Wu, Liang; Wei, Hanlin; Chen, Jianzhong; Zhang, Wanbin

doi:10.6023/cjoc202106021

Cited by 11 publications

(3 citation statements)

References 196 publications

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“…In 2017, it was reported that the nickel complex could be used to catalyze the azide−alkyne cycloaddition (NiAAC) to generate 1,5-disubstitued 1,2,3-triazoles at room temperature. 60 Attracted by this new effective reaction and robust Ni catalyst, 61 we, as a group focusing on the development of new efficiently alkyne-based click polymerization, anticipated that it could be developed into a new click polymerization. Indeed, through systematic investigation, a highly efficient nickel-catalyzed azide−alkyne click polymerization (NiAACP) was successfully established.…”

Section: ■ Introductionmentioning

confidence: 99%

Nickel-Catalyzed Azide–Alkyne Click Polymerization toward 1,5-Regioregular Polytriazoles

Huang,

Liu,

Qin

et al. 2023

Macromolecules

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Section: ■ Introductionmentioning

confidence: 99%

Nickel-Catalyzed Azide–Alkyne Click Polymerization toward 1,5-Regioregular Polytriazoles

Huang,

Liu,

Qin

et al. 2023

Macromolecules

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“…However, because of the poor leaving ability of the hydroxyl group, direct displacement of the hydroxyl group is laborious, and only π-activated allylic and benzylic alcohols are effective for transition-metal-catalyzed arylation reactions. Therefore, alternatively, activated derivatives of simple aliphatic alcohols are applied in several transition-metal-catalyzed deoxygenative C(sp 3 )–C(sp 2 ) couplings with aryl halides. Apparently, these protocols require preanchored activating groups, and their synthesis and purification sequences increase the operational complexity and cost.…”

mentioning

confidence: 99%

Dehydroxylative Arylation of Alcohols via Paired Electrolysis

et al. 2022

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Nonactivated alcohols along with arene compounds are used in electrochemical dehydroxylative arylation for constructing C(sp 3 )−C(sp 2 ) bonds. The P III reagent undergoes single-electron anodic oxidation to form its radical cation, which reacts with the alcohol to produce an alkoxytriphenylphosphine radical. Through spontaneous βscission of the phosphoranyl radical, the C−O bond is cleaved to form an alkyl radical species, which couples with the radical anion generated by cathodic reduction of the electron-poor arene to afford the dehydroxylative arylated product.M ethods to construct C(sp 3 )−C(sp 2 ) bonds are among the most essential reactions in organic chemistry. Because of the characteristics of alcohols, including great availability, high stability, low cost, and benign nature, the dehydroxylative reaction of alcohols with aromatic compounds could be an ideal method to build C(sp 3 )−C(sp 2 ) bonds. Among them, Friedel−Crafts alkylation of aromatic substrates with alcohols through an S N 1 substitution pathway has gained considerable importance. 1 However, the reaction has disadvantages, including the need for a stoichiometric amount of a strong Lewis acid, rearrangement of carbocations, failure with electron-poor arenes, and undesired polyalkylation. Therefore, tremendous efforts have been made in order to develop dehydroxylative C(sp 3 )−C(sp 2 ) couplings of nonactivated free alcohols with more broad substrate scope under mild conditions. Metal catalysis 2 with the power to break C−X bonds and build C−C bonds has been introduced to the dehydroxylative reaction of alcohols with aromatic compounds. However, because of the poor leaving ability of the hydroxyl group, direct displacement of the hydroxyl group is laborious, and only π-activated allylic 3 and benzylic alcohols 4 are effective for transition-metal-catalyzed arylation reactions. Therefore, alternatively, activated derivatives of simple aliphatic alcohols are applied in several transition-metal-catalyzed deoxygenative C(sp 3 )−C(sp 2 ) couplings 5 with aryl halides. Apparently, these protocols require preanchored activating groups, and their synthesis and purification sequences increase the operational complexity and cost.Recently, several protocols have been reported for deoxygenative arylation by transition metal catalysis with alkyl halide intermediates generated in situ from alcohols (Scheme 1A). In 2021, the Li group 6 developed a dehydroxylative method to build C(sp 3 )−C(sp 2 ) bonds with a Ni-enabled electrochemical redox approach. This protocol involves in situ conversion of primary or secondary alcohols into alkyl bromides and subsequent cross-electrophile coupling

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“…17 A nickel-catalyzed cross-coupling reaction was proposed via a one-step alcohol deoxygenation pathway, whereas the method did not tolerate ketone derivatives (Scheme 1B). 18 In our own studies, we reasoned that transition metal catalysts could lower the activation energy of ketones as well as hydrazone, and therefore can achieve direct deoxygenation under mild conditions.…”

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confidence: 99%