Nickel-catalysed regio- and stereoselective acylzincation of unsaturated hydrocarbons with organozincs and CO

Weng, Yangyang; Zhang, Yetong; Turlik, Aneta; Wu, Xianqing; Li, Haiyan; Fei, Fan; Yao, Yongkang; Wang, Chenglong; Guo, Zhiqian; Qü, Jingping; Houk, K. N.; Chen, Yifeng

doi:10.1038/s44160-022-00208-z

Cited by 11 publications

(6 citation statements)

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“…Based on the previous studies, [ 11 ] a plausible mechanism for this nickel‐catalyzed acylzincation‐initiated cyclization reaction of styrene is proposed in Scheme 3. Transmetallation of the nickel catalyst and alkyl zinc reagents affords alkyl nickel species A , which undergoes selective 1,1‐insertion into CO to provide acyl nickel intermediate B .…”

Section: Resultsmentioning

confidence: 99%

“…[ 5‐10 ] Nevertheless, the carbonylation reaction involving acylmetallation of alkene process has largely stagnated. Recently, we have disclosed a unique nickel‐catalyzed chemo‐, regio‐ and stereoselective acylzincation of unsaturated hydrocarbons with organozinc reagent under atmospheric CO gas through the in‐situ generation of catalytic acylnickel species, [ 11a ] which represents a new paradigm of carbometallation reaction (Scheme 1a). The utilization of a nickel catalyst with a multidentate nitrogen‐based ligand obviates the toxic effect of CO on the nickel center.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO^†

Wang,

Liu,

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryTransition metal‐catalyzed carbometallation of unsaturated hydrocarbons constitutes one of the most efficient synthetic methodologies for the construction of C─C bond. Recently, the incorporation of organometallic reagent with the CO gas as a nucleophilic acyl synthon could enable the acylmetallation reaction, which greatly increase the horizon of carbometallation chemistry. Herein we report a nickel‐catalyzed regiodivergent acylzincation of o‐cyano cinnamate ester and o‐cyano styrene, in which the cyano moiety intramolecularly captures zinc intermediates to trigger the tandem cyclization process. This protocol features with mild conditions, broad substrate scope and excellent functional group tolerance, thus affording a diverse array of highly functionalized carbocyclic compounds.This article is protected by copyright. All rights reserved.

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Section: Resultsmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO^†

Wang,

Liu,

et al. 2023

Chin. J. Chem.

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“…Scheme 1 Alkoxycarbonylation of aromatic iodides with alcohols Scheme 2 Carbonylation of cyclopropanol with benzyl bromide Scheme 3 Mechanism of carbonylation of cyclopropanol with benzyl bromide oxabicyclic alkenes and α,β-unsaturated ketones with acyl nucleophiles under mild conditions. [13] In the same year, they also described a nickel-catalyzed carbonylative reaction between allylic alcohols and organoalanes with CO (Scheme 4). [14] To suppress the carbonylative dimerization of allylic alcohols, organoalane is selected as the activator to construct the coupling system.…”

Section: Nickel Catalyzed Carbonylation With Co Gas As the Carbonyl S...mentioning

confidence: 99%

Recent Advances in Nickel Catalyzed Carbonylative Reactions via the Insertion of Carbon Monoxide^†

Chen,

Lian

2023

Chin. J. Chem.

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Comprehensive SummaryCarbonyl compounds have attracted considerable attention due to their extensive applications in drug discovery. Furthermore, they are important synthetic intermediates for the construction of carbon‐carbon and carbon‐heteroatom bonds. Transition‐metal‐catalyzed carbonylation via the insertion of CO is one of the most efficient and straightforward strategies to access carbonyl compounds. However, most of the transition‐metal‐catalyzed carbonylative reactions require expensive and toxic noble‐metal catalysts. Therefore, there is a growing demand for the exploration of nickel‐catalyzed carbonylative reactions via the insertion of CO due to the earth abundance and low cost of nickel. Compared with the well‐established palladium‐catalyzed carbonylative reactions, nickel‐catalyzed analogous transformations have been relatively underdeveloped. This is primarily because CO strongly binds to nickel, often resulting in catalyst poisoning. In recent years, some research groups have focused on using CO surrogates or NN2 pincer nickel catalyst to circumvent the formation of Ni(CO)4. Nickel‐catalyzed carbonylation has been applied in the construction of carbonyl‐containing compounds, such as ketones, carboxylic acids, thioesters, acyl chloride and carboxamides.

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“…15 The T-S rearrangement 11 can also produce arylated products via a 2-electron pathway and is similar to S N Ar reactions. While Truce-Smiles rearrangement reactions generally require electron-withdrawing groups, the original work by Truce 16 and recent studies by Clayden 17,18 and others 19,20 have demonstrated that electron-withdrawing groups are not always needed.…”

Section: Introductionmentioning

confidence: 99%

A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe₃)₂

Zhou,

Jin,

Xiang

et al. 2023

Org. Chem. Front.

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Nickel-catalysed regio- and stereoselective acylzincation of unsaturated hydrocarbons with organozincs and CO

Cited by 11 publications

References 82 publications

Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO^†

Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO^†

Recent Advances in Nickel Catalyzed Carbonylative Reactions via the Insertion of Carbon Monoxide^†

A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe₃)₂

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Nickel-catalysed regio- and stereoselective acylzincation of unsaturated hydrocarbons with organozincs and CO

Cited by 11 publications

References 82 publications

Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO†

Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO†

Recent Advances in Nickel Catalyzed Carbonylative Reactions via the Insertion of Carbon Monoxide†

A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe3)2

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Product

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Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO^†

Nickel‐Catalyzed Regiodivergent Acylzincation of Styrenes with Organozincs and CO^†

Recent Advances in Nickel Catalyzed Carbonylative Reactions via the Insertion of Carbon Monoxide^†

A regiodivergent Truce–Smiles rearrangement: a strategy for the synthesis of arylated indoles promoted by KN(SiMe₃)₂