Halogen-bond-promoted direct cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoates with coumarins/quinolinones

Pu, Guoliang; Song, Shi-Yuan; Yang, Jian; Guo, Peng; Jia, Jia; Liu, Peijun; Li, Xuefei; Liu, Ping; He, Chun-Yang

doi:10.1039/d4qo00484a

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00484a

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Halogen-bond-promoted direct cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoates with coumarins/quinolinones

Guoliang Pu,

Shi-Yuan Song,

Jian Yang

et al.

Abstract: Herein, we developed a practical method for the direct cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoate with coumarins/quinolinones, leveraging a halogen bond as the pivotal non-covalent interaction. Employing this protocol, a library of...

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Cited by 3 publications

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A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides

Tasnim,

Shafiei,

Laminack

et al. 2024

J. Org. Chem.

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A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides

Tasnim,

Shafiei,

Laminack

et al. 2024

J. Org. Chem.

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Catalytic reduction of trifluoromethylated alkyl bromides and synthesis of alkylated heterocycles under visible light irradiation: synergetic action of a halogen bond and Ni catalysis

Wang,

Guo,

et al. 2024

Org. Chem. Front.

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A Continuous-Flow Protocol for the Synthesis of Alkenyl Thioethers Based on the Photochemical Activation of Halogen-Bonding Complexes

Plaza,

Piedra,

Valdés

2024

Synlett

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We report a useful flow protocol for the preparation of alkenyl thioethers from alkenyl bromides and thiols in basic media with visible-light irradiation. The reactions exhibit a wide functional-group tolerance, proceed under mild conditions, are stereoselective, and do not require the use of catalysts. The transformations can be successfully scaled up to 5 mmol scale without compromising the yield. The key to the success of these reactions is the photochemical excitation of halogen-bonding complexes to form alkenyl and sulfur-centered radicals, a protocol recently developed in our laboratories.

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Halogen-bond-promoted direct cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoates with coumarins/quinolinones

Abstract: Herein, we developed a practical method for the direct cross-coupling of ethyl 3-bromo-3-alkyl-2,2-difluoropropanoate with coumarins/quinolinones, leveraging a halogen bond as the pivotal non-covalent interaction. Employing this protocol, a library of...

Cited by 3 publications

References 42 publications

A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides

A Dual Catalytic Approach for the Halogen-Bonding-Mediated Reductive Cleavage of α-Bromodifluoroesters and Amides

Catalytic reduction of trifluoromethylated alkyl bromides and synthesis of alkylated heterocycles under visible light irradiation: synergetic action of a halogen bond and Ni catalysis

A Continuous-Flow Protocol for the Synthesis of Alkenyl Thioethers Based on the Photochemical Activation of Halogen-Bonding Complexes

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