Electrochemically enabled cobalt catalyzed enantioselective C–H acyloxylation of aryl phosphamide with carboxylic acid

Xia, Xuying; Zheng, Changdi; Hang, Yunfei; Guo, Jiyuan; Liu, Tao; Song, Dingguo; Chen, Zhiwei; Zhong, Weihui; Ling, Fei

doi:10.1039/d4gc01404a

Green Chem.

2024

DOI: 10.1039/d4gc01404a

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Electrochemically enabled cobalt catalyzed enantioselective C–H acyloxylation of aryl phosphamide with carboxylic acid

Xuying Xia,

Changdi Zheng,

Yunfei Hang

et al.

Abstract: We described here the first example of cobalt-electro-catalyzed enantioselective C–H acyloxylation of arylphosphinamides with carboxylic acids to generate P-stereogenic scaffolds.

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Cited by 5 publications

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Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation

Xu,

Zheng,

Lin

et al. 2024

Angewandte Chemie

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The control of enantioselectivity in radical cation reactions presents long‐standing challenges, despite a few successful examples. We introduce a novel strategy of asymmetric counteranion‐directed electrocatalysis to address enantioselectivity in radical cation chemistry. This concept has been successfully demonstrated in two reactions: an asymmetric dehydrogenative indole‐phenol [3+2] coupling and an atroposelective C−H/N−H dehydrogenative coupling. These reactions have enabled the synthesis of benzofuroindolines and C−N axially chiral indoles with high yields and excellent enantiomeric excesses. Detailed mechanistic studies confirmed a radical‐radical coupling mechanism. Moreover, density functional theory (DFT) calculations supported the indole radical cation as the pivotal intermediate, rather than a neutral indolyl radical, shedding new light on the underlying processes driving these reactions.

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Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation

Xu,

Zheng,

Lin

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation

Xu,

Zheng,

Lin

et al. 2024

Angew Chem Int Ed

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Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

Liu,

Tang,

Guo

et al. 2024

Org. Lett.

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We present here a novel paired electrocatalysis-enabled convenient synthesis of the (E)-vinyl sulfoximines through the cross-coupling reaction of sulfinamides and olefins. This protocol showed a broad substrate scope and excellent E selectivity of products under metal-and oxidant-free conditions. A preliminary mechanistic study suggested that fluorinated sulfoximine generated from anodic oxidation of sulfinamide was the key intermediate that was then converted into the sulfonimidoyl radical at the cathode with the help of DBU in this reaction.

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Electrochemically enabled cobalt catalyzed enantioselective C–H acyloxylation of aryl phosphamide with carboxylic acid

Abstract: We described here the first example of cobalt-electro-catalyzed enantioselective C–H acyloxylation of arylphosphinamides with carboxylic acids to generate P-stereogenic scaffolds.

Cited by 5 publications

References 64 publications

Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation

Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation

Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation

Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

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