A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates DOI Creative Commons
Yao Zhang, Jiawei Ma, Jian Chen

et al.

Chem, Journal Year: 2021, Volume and Issue: 7(11), P. 3171 - 3188

Published: Nov. 1, 2021

Language: Английский

Nickel-Catalyzed Difluoroalkylation–Alkylation of Enamides DOI
Chang Xu, Zhifang Yang, Lun An

et al.

ACS Catalysis, Journal Year: 2019, Volume and Issue: 9(9), P. 8224 - 8229

Published: July 25, 2019

Nickel-catalyzed carbodifunctionalization of alkenes is an efficient strategy for the construction C–C bonds. However, applications in dialkylation remain underdeveloped due to difficulties suppressing competitive side reactions. We now describe a nickel-catalyzed tandem reaction by difluoroalkylation–alkylation N-vinyl 2-pyrrolidinone with difluoroalkyl bromides and dialkylzinc reagents. The can also extend N-vinyloxazolidinone N-vinylacetamide. This proceeds smoothly under mild conditions good functional group tolerance, providing straightforward access gem-difluoroalkylated derivatives that are interest medicinal chemistry.

Language: Английский

Citations

87
Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes DOI Creative Commons
Guojiao Wu, Axel Jacobi von Wangelin

Chemical Science, Journal Year: 2018, Volume and Issue: 9(7), P. 1795 - 1802

Published: Jan. 1, 2018

Stereoselective additions of functionalized reagents to unsaturated hydrocarbons are attractive due the high atom economy, modularity and rapid generation complexity. We report a stereoselective cobalt-catalyzed (E)-halofluoroalkylation alkynes/alkenes that under mild conditions (2 mol% cat., 20 °C, acetone/water, 3 h). This reaction operates via radical chain mechanism involving terminal halogen transfer which obviates need for stoichiometric sacrificial reductant.

Language: Английский

Citations

86
Nickel-Catalyzed Carbonylation of Difluoroalkyl Bromides with Arylboronic Acids DOI

Haiyang Zhao,

Xing Gao, Shu Zhang

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(4), P. 1031 - 1036

Published: Jan. 31, 2019

A nickel-catalyzed carbonylative difluoroalkylation reaction with arylboronic acids under 1 atm of CO has been developed. The proceeds mild conditions high efficiency and functional group tolerance. Preliminary mechanistic studies reveal that the arylacyl nickel complex is key intermediate to circumvent formation labile fluoroacyl nickel, bimetallic oxidative addition likely step facilitate catalytic cycle.

Language: Английский

Citations

85
Silver‐Catalyzed Decarboxylative Allylation of Difluoroarylacetic Acids with Allyl Sulfones in Water DOI
Xiang Li, Ruihong Zhang, Xiaofei Zhang

et al.

Chemistry - An Asian Journal, Journal Year: 2020, Volume and Issue: 15(7), P. 1175 - 1179

Published: Feb. 14, 2020

A practical silver-catalyzed decarboxylative allylation of α,α-difluoroarylacetic acids with allyl sulfones is described, which provides a variety β,β-difluorinated alkenes in good yields. Notably, the reaction proceeds smoothly water functional group tolerance. The practicality and synthetic value this process was demonstrated by scaled-up experiment elaboration products via reduction or Heck reaction. Primary mechanism investigations suggest that radical might be involved.

Language: Английский

Citations

81
A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates DOI Creative Commons
Yao Zhang, Jiawei Ma, Jian Chen

et al.

Chem, Journal Year: 2021, Volume and Issue: 7(11), P. 3171 - 3188

Published: Nov. 1, 2021

Language: Английский

Citations

77