Rh2(II)-Catalyzed Selective C(sp3)-H Bond Electrophilic Amination of Aryl Azide-Tethered 1,3-Dicarbonyl Compounds

被引：4

作者：

Donthoju, Ashok ^{[1
,2
]}

Phanindrudu, Mandalaparthi ^{[1
]}

Ellandula, Sushma ^{[1
]}

Lal, Malavath Ratan ^{[1
]}

Nanubolu, Jagadeesh Babu ^{[2
,3
]}

Chegondi, Rambabu ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Chem Technol CSIR IICT, Dept Organ Synth & Proc Chem, Hyderabad 500007, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] CSIR Indian Inst Chem Technol CSIR IICT, Dept Analyt & Struct Chem, Hyderabad 500007, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 41期

关键词：

ALPHA-AMINATION; FUNCTIONALIZATION; DERIVATIVES; CATALYSTS; ROUTE;

D O I：

10.1021/acs.orglett.3c03067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the accomplishment of Rh2(II)-catalyzed intramolecular amination of aryl azide-tethered 1,3-dicarbonyls to access privileged heterocyclic scaffolds with exclusive diastereoselectivity under simple reaction conditions. This method also allows an unconventional direct alpha-amination at electron-deficient C-(sp3)-H bonds of aryl azide-tethered 1,3-diketones to afford fused 2-azatricyclo-[4.4.0.02,8]-decanones and 2,2-disubstituted indolines, which are present in several biologically active alkaloids. Kinetic isotope experiments revealed that the nucleophilic addition of enol pi-bonds on the transient electrophilic rhodium-nitrenoid intermediate enables C-N bond formation.

引用

页码：7589 / 7594

页数：6

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