Shu-Ying Ding

Anhui Agricultural University

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Zhenhua Gu

University of Science and Technology of China

Z. Y. Pei

Guangzhou University

Fang Wei

Anhui Agricultural University

Chuan‐Zhi Yao

Anhui Agricultural University

Meng‐Lan Shen

Anhui Agricultural University

Hua‐Jie Jiang

Anhui Agricultural University

Jie Yu

Anhui Agricultural University

Qiankun Li

Anhui Agricultural University

Yan-Dong Meng

Anhui Agricultural University

Shiqing Han

Nanjing Tech University

Cooperative Institutions

Anhui Agricultural University

University of Science and Technology of China

Hefei National Center for Physical Sciences at Nanoscale

Nanjing Tech University

Chinese Academy of Sciences

Hefei University

University of California, Berkeley

Shanghai Institute of Organic Chemistry

Zhengzhou University

Southern University of Science and Technology

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Dioxygen as Oxidant for the Synthesis of Indoles by Pd-Catalyzed C-H Activation

Synfacts (2009)

Zhichao Shi Chun Zhang Sifan Li Dalong Pan Shu-Ying Ding

Jiao and co-workers reported the synthesis of indoles from anilines and alkynes by a C-H activation process catalyzed by Pd(OAc)2 which uses dioxygen as the oxidant in the catalytic cycle. The best results were obtained when using a mixture of DMA and pivaloic acid (PivOH) as the solvent. The scope of the reaction was well studied. Thus, both EWGs and EDGs in the starting anilines were well tolerated whereas only electron-deficient alkynes afforded the corresponding indoles in modest to good yields. In addition, N-monosubstituted anilines participated efficiently in the reaction.

Catalytic cycle

Reaction conditions

10.1055/s-0029-1217452

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Asymmetric S‐Arylation of Sulfenamides to Access Axially Chiral Sulfilimines Enabled by Anionic Stereogenic‐at‐Cobalt(III) Complexes

Angewandte Chemie International Edition (2024)

Hua‐Jie Jiang Fang Wei Yonggang Meng Shu-Ying Ding Jian‐Zhong Wang

An efficient enantioselective coupling reaction between sulfenamides and cyclic diaryliodonium salts is established via adaptive Cu/anionic stereogenic‐at‐Co(III) complex combined catalysis, precisely synthesizing a broad range of axially chiral sulfilimines with excellent enantioselectivities, diastereoselectivities, regioselectivities, and chemoselectivities (67 examples under same conditions, up to 98% ee). The following thermodynamically controlled pyramidal inversion enables efficient stereodivegent synthesis of all four stereoisomers. Mechanistic studies suggest that anionic stereogenic‐at‐cobalt(III) complexes serve as counteranions of diaryliodonium and anionic ligand of Cu(I) catalyst simultaneously, which could be regarded as an explanation for outstanding selectivities.

Stereocenter

10.1002/anie.202419596

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Asymmetric S‐Arylation of Sulfenamides to Access Axially Chiral Sulfilimines Enabled by Anionic Stereogenic‐at‐Cobalt(III) Complexes

Angewandte Chemie (2024)

Hua‐Jie Jiang Fang Wei Yan-Dong Meng Shu-Ying Ding J.J. Wang

Stereocenter

10.1002/ange.202419596

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Elemental Sulfur-Mediated Decarboxylative Redox Cyclization Reaction: Copper-Catalyzed Synthesis of 2-Substituted Benzothiazoles

Synlett (2017)

Xin Wang Xiaotong Li Renhe Hu Yang Zhao Ren Gu

A S8-mediated directed decarboxylative redox-cyclization strategy for the synthesis of 2-substituted benzothiazoles from o-iodoanilines, arylacetic acids, and elemental sulfur catalyzed by cheap copper metal has been developed. This reaction is operationally simple, ligand-free, compatible with a wide range of functional groups, and provides the desired products in good to excellent yields. In addition, a gram-scale experiment was carried out to furnish PMX 610, an antitumor drug.

Decarboxylation

10.1055/s-0036-1589112

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Citations (18)