Auxiliary-controlled regiodivergent NiH-catalyzed <i>gem</i>-difluoroallylation of alkenyl amines <i>via</i> defluorinative olefin cross-coupling

Zhu, Lin; Huang, Jie; Meng, Fanling; Tan, Ziyun; Meng, Xiao; Xiao, Yang; Zhang, Lanlan; Li, Wenyi; Wang, Chao

doi:10.1039/d3qo01053h

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01053h

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Auxiliary-controlled regiodivergent NiH-catalyzed gem-difluoroallylation of alkenyl amines via defluorinative olefin cross-coupling

Lin Zhu,

Jie Huang,

Fanling Meng

et al.

Abstract: A NiH-catalyzed migratory and nonmigratory gem-difluoroallylation reaction of alkenyl amines with trifluoromethyl alkenes has been developed by judicious choice of the directing groups. The reaction incorporates gem-difluoroalkene motifs into aliphatic...

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2024

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Cited by 7 publications

References 76 publications

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Electrochemical Decarboxylative Trifluoromethylation of Cinnamic Acids Revisited: A Combined Experimental and Computational Study

Yamamoto,

Goto,

Uchida

et al. 2024

Chemistry An Asian Journal

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beta‐(Trifluoromethyl)styrenes are potentially useful building blocks for the synthesis of organofluorine compounds because their electron‐deficient C=C double bonds can undergo diverse transformations. One of the most practical methods for preparing b‐(trifluoromethyl)styrenes is the decarboxylative trifluoromethylation of readily available cinnamic acid derivatives using the Langlois reagent as a less expensive trifluoromethyl source. We revisited the electrochemical decarboxylative trifluoromethylation of cinnamic acid derivatives to identify modified conditions that reduce the loading of the Langlois reagent without additional additives. The reaction mechanism was computationally investigated to gain insight into the dependence of the product yields on the aryl terminal groups. The synthetic utility of the obtained b‐(trifluoromethyl)styrenes was demonstrated by their transformation into 4‐aryl‐3‐(trifluoromethyl)pyrrolidines.

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Electrochemical Decarboxylative Trifluoromethylation of Cinnamic Acids Revisited: A Combined Experimental and Computational Study

Yamamoto,

Goto,

Uchida

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

Ligand-controlled NiH-catalyzed regiodivergent hydroalkylation of 2-alkenylazaarenes

Shao,

Chi,

Liang

2024

Sci. China Chem.

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Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction

Han,

Zeng,

Fei

et al. 2024

Chinese Chemical Letters

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Auxiliary-controlled regiodivergent NiH-catalyzed gem-difluoroallylation of alkenyl amines via defluorinative olefin cross-coupling

Abstract: A NiH-catalyzed migratory and nonmigratory gem-difluoroallylation reaction of alkenyl amines with trifluoromethyl alkenes has been developed by judicious choice of the directing groups. The reaction incorporates gem-difluoroalkene motifs into aliphatic...

Cited by 7 publications

References 76 publications

Electrochemical Decarboxylative Trifluoromethylation of Cinnamic Acids Revisited: A Combined Experimental and Computational Study

Electrochemical Decarboxylative Trifluoromethylation of Cinnamic Acids Revisited: A Combined Experimental and Computational Study

Ligand-controlled NiH-catalyzed regiodivergent hydroalkylation of 2-alkenylazaarenes

Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction

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