Rh(III)-Catalyzed Diastereo- and Enantioselective Regiodivergent (Hetero)Arylamidation of (Homo)Allylic Sulfides

被引：3

作者：

Jia, Xiaoyan ^{[1
,2
]}

Hao, Gui-Lin ^{[3
]}

Feng, Mengxia ^{[1
,2
]}

Jiang, Huanfeng ^{[1
,2
]}

Wang, Shou-Guo ^{[3
]}

Huang, Liangbin ^{[1
,2
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, State Key Lab Pulp & Paper Engn, Guangzhou 510640, Peoples R China

[2] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Peoples R China

[3] Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2024年 / 146卷 / 14期

基金：

中国国家自然科学基金;

关键词：

CATALYZED 3-COMPONENT CARBOAMINATION; C-H BONDS; INTERMOLECULAR CARBOAMINATION; UNACTIVATED ALKENES; SUBSTITUTION; DERIVATIVES; ARYLATION; REAGENTS; OLEFINS; ACCESS;

D O I：

10.1021/jacs.3c14041

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium-catalyzed 3-component conjunctive diastereo- and regioselective arylamidation of (homo)allylic sulfides, organon boronic acids, and dioxazolones is reported. These reactions deliver the 1,2-insertion and 2,1-insertion arylamidation products, respectively, for allylic sulfides and homoallylic sulfides. The enantioselective arylamidation of terminal and internal allylic sulfides is achieved, furnishing various 1,3-N,S compounds featuring one or two contiguous stereocenters in high yields and with high diastereo- and enantioselectivities. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining steps induced by the native and easily removable sulfide group.

引用

页码：9768 / 9778

页数：11

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