Divergent α-functionalization of cyclic amines via ring construction by molecular O2 oxidized dearomatization and ring deconstruction by aromatization-driven C-C σ-bond cleavage

被引：18

作者：

Hu, Fangzhi ^{[1
]}

Wang, Liang ^{[1
,2
]}

Ge, Chunyan ^{[1
]}

Li, Xinyao ^{[1
]}

Ding, Zhanshuai ^{[1
]}

Xu, Lubin ^{[1
]}

Li, Shuai-Shuai ^{[1
,2
]}

机构：

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

[2] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Zhengzhou Rd 53, Qingdao 266042, Peoples R China

来源：

GREEN CHEMISTRY | 2021年 / 23卷 / 15期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ASYMMETRIC DEAROMATIZATION; H FUNCTIONALIZATION; C(SP(3))-H FUNCTIONALIZATION; COUPLING REACTION; NITROGEN; ARYLATION; ADJACENT; CASCADE; TETRAHYDROISOQUINOLINES; ACTIVATION;

D O I：

10.1039/d1gc00941a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient approach to achieve the divergent alpha-C(sp(3))-H functionalization of cyclic amines through a rationally designed ring construction and ring deconstruction strategy was developed. A variety of spiro cyclohexadienone decorated cyclic amines were obtained via ring construction by molecular O-2 oxidized dearomatization/cyclization. In addition, the sequential alpha-C(sp(3))-H bond functionalization of cyclic amines was achieved via ring deconstruction through aromatization-driven C-C bond cleavage/intermolecular functionalization with the addition of diverse Grignard reagents or NaBD4.

引用

页码：5535 / 5541

页数：7

共 65 条

[1] Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences [J].

Atzrodt, Jens ;

Derdau, Volker ;

Kerr, William J. ;

Reid, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (07) :1758-1784

[2] Controllable Syntheses of Spiroindolenines and Benzazepinoindoles via Hexafluoroisopropanol-Mediated Redox-Neutral Cascade Process [J].

Bai, Guangxian ;

Dong, Fengying ;

Xu, Lubin ;

Liu, Yongjun ;

Wang, Liang ;

Li, Shuai-Shuai .

ORGANIC LETTERS, 2019, 21 (16) :6225-6230

[3] Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water [J].

Basle, Olivier ;

Li, Chao-Jun .

GREEN CHEMISTRY, 2007, 9 (10) :1047-1050

[4] Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes [J].

Cabrera, Pablo J. ;

Lee, Melissa ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (16) :5599-5606

[5] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].

Campos, Kevin R. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084

[6] Photoelectrocatalytic phenol oxidation employing nitrogen doped TiO2-rGO films as photoanodes [J].

Carreno-Lizcano, M., I ;

Gualdron-Reyes, Andres F. ;

Rodriguez-Gonzalez, V ;

Pedraza-Avella, J. A. ;

Nino-Gomeza, M. E. .

CATALYSIS TODAY, 2020, 341 :96-103

[7] Efficient construction of tetrahydroquinolines via fluorinated alcohol mediated cascade [1,5]-hydride transfer/cyclization [J].

Chen, Chunqi ;

Xu, Lubin ;

Wang, Liang ;

Li, Shuai-Shuai .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (39) :7109-7114

[8] Organocatalytic Atroposelective Arylation of 2-Naphthylamines as a Practical Approach to Axially Chiral Biaryl Amino Alcohols [J].

Chen, Ye-Hui ;

Qi, Liang-Wen ;

Fang, Fang ;

Tan, Bin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16308-16312

[9] Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities [J].

Cushnie, T. P. Tim ;

Cushnie, Benjamart ;

Lamb, Andrew J. .

INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2014, 44 (05) :377-386

[10] Hydride transfer enabled switchable dearomatization of indoles in the carbocyclic ring and the pyrrole ring [J].

Duan, Kang ;

Shi, Hongjin ;

Wang, Lin-Xuan ;

Li, Shuai-Shuai ;

Xu, Lubin ;

Xiao, Jian .

ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) :2511-2517

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