Metal-Free Catalytic Approach for Allylic C-H Amination Using N-Heterocycles via sp3 C-H Bond Activation

被引：36

作者：

Sun, Jinwei ^{[1
]}

Wang, Yi ^{[1
]}

Pan, Yi ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 18期

基金：

中国国家自然科学基金;

关键词：

EFFICIENT SYNTHESIS; DEHYDROGENATIVE FUNCTIONALIZATION; ORGANOCATALYTIC AMINATION; ALLYLAMINE DERIVATIVES; COUPLING REACTIONS; TERMINAL ALKENES; SIMPLE OLEFINS; ALKYLATION; OXIDATION; STRATEGY;

D O I：

10.1021/acs.joc.5b01383

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile metal-free synthesis of allylic N-heterocycles has been developed using a TBAI/TBHP oxidation system. This general protocol could be applied for the C-N bond formation of electron-deficient phthalimides, imidazoles, triazoles, and sulfonamides with cyclic and acylic olefins. The practical use of the method is demonstrated by the amidation of functionalized biologically active substrates.

引用

页码：8945 / 8950

页数：6

共 50 条

[1] Catalytic Metal-free Allylic C-H Amination of Terpenoids
Teh, Wei Pin
Obenschain, Derek C.
Black, Blaise M.
Michael, Forrest E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (39) : 16716 - 16722
[2] Palladium-Catalyzed Allylic Amidation with N-Heterocycles via sp3 C-H Oxidation
Vemula, Sandeep R.
Kumar, Dinesh
Cook, Gregory R.
ACS CATALYSIS, 2016, 6 (08): : 5295 - 5301
[3] Metal-free oxidative C-C bond formation of active methylenic sp3 C-H bonds with benzylic sp3 C-H and allylic sp3 C-H bonds mediated by DDQ
Ramesh, D.
Ramulu, U.
Rajaram, S.
Prabhakar, P.
Venkateswarlu, Y.
TETRAHEDRON LETTERS, 2010, 51 (37) : 4898 - 4903
[4] Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds
Zhao, Dan
Wang, Teng
Li, Jian-Xin
CHEMICAL COMMUNICATIONS, 2014, 50 (49) : 6471 - 6474
[5] Metal-Free Intermolecular Allylic C-H Amination of Alkenes Using Primary Carbamates
Obenschain, Derek C.
Tabor, John R.
Michael, Forrest E.
ACS CATALYSIS, 2023, 13 (07) : 4369 - 4375
[6] Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines
Evoniuk, Christopher J.
Gomes, Gabriel dos Passos
Hill, Sean P.
Fujita, Satoshi
Hanson, Kenneth
Alabugin, Igor V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) : 16210 - 16221
[7] Fe-Catalyzed α-C(sp3)-H Amination of N-Heterocycles
Geraci, Andrea
Baudoin, Olivier
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (05)
[8] Metal-Free C-H Amination for Indole Synthesis
Jang, Young Ho
Youn, So Won
ORGANIC LETTERS, 2014, 16 (14) : 3720 - 3723
[9] Synthesis of Imidazo[1,5-a]quinolines via Metal-Free Oxidative Amination of sp3 C-H Bonds
Liu, Huanhuan
Wang, Xinfeng
Ma, Chen
SYNTHESIS-STUTTGART, 2018, 50 (14): : 2761 - 2767
[10] Catalytic Intermolecular C(sp3)-H Amination: Selective Functionalization of Tertiary C-H Bonds vs Activated Benzylic C-H Bonds
Brunard, Erwan
Boquet, Vincent
Van Elslande, Elsa
Saget, Tanguy
Dauban, Philippe
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (17) : 6407 - 6412

← 1 2 3 4 5 →