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

共 44 条

[41] 4-Amino-2,1,3-benzothiadiazole as a Removable Bidentate Directing Group for the Pd(II)-Catalyzed Arylation/Oxygenation of sp2/sp3 β-C-H Bonds of Carboxamides
Reddy, Chennakesava
Bisht, Narendra
Parella, Ramarao
Babu, Srinivasarao Arulananda
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) : 12143 - 12168
[42] Rh(III)-Catalyzed Sequential ortho-C-H Bond Annulation and Desulfonylation of 3-Aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides: Access to 1-Aminoisoquinolines
Ajay, Chidrawar
Balasubramanian, Sridhar
Reddy, Basi V. Subba
CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (23)
[43] Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1H-benzo[d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage
Xu, Cheng
Yin, Guodong
Jia, Feng-Cheng
Wu, Yan-Dong
Wu, An-Xin
ORGANIC LETTERS, 2021, 23 (07) : 2559 - 2564
[44] Ru(II)/Ir(III)-Catalyzed C-H Bond Activation/Annulation of Cyclic Amides with 1,3-Diketone-2-diazo Compounds: Facile Access to 8H-Isoquinolino[1,2-b]quinazolin-8-ones and Phthalazino[2,3-a]cinnoline-8,13-diones
Cai, Panyuan
Zhang, Enshen
Wu, Yinsong
Fang, Taibei
Li, Qianqian
Yang, Chen
Wang, Jian
Shang, Yongjia
ACS OMEGA, 2018, 3 (11): : 14575 - 14584

← 1 2 3 4 5 →