Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier

被引：85

作者：

Chen, Xiu-Wen ^{[1
]}

Zhao, He ^{[1
]}

Chen, Chun-Lian ^{[1
]}

Jiang, Huan-Feng ^{[1
]}

Zhang, Min ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510641, Guangdong, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 45期

基金：

中国国家自然科学基金;

关键词：

1,8-naphthyridines; hydrogen donor; iridium catalysis; tetrahydroquinolines; transfer hydrogenative coupling; C-H ACTIVATION; PLANAR CHIRAL FERROCENES; REGIOSELECTIVE SYNTHESIS; TRIAZOLE ASSISTANCE; ALKYLATION; METAL; LIGANDS; ALKENYLATION; ARYLATION; CATALYSIS;

D O I：

10.1002/anie.201707702

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general catalytic hydrogen transfer-mediated alpha-functionalization of 1,8-naphthyridines is reported for the first time that benefits from a hydrogen transfer-mediated activation mode for non-activated pyridyl cores. The pyridyl a-site selectively couples with the C8-site of various tetrahydroquinolines (THQs) to afford novel alpha-functionalized tetrahydro 1,8-naphthyridines, a class of synthetically useful building blocks and potential candidates for the discovery of therapeutic and bio-active products. The utilization of THQs as inactive hydrogen donors (HDs) appears to be a key strategy to overcome the over-hydrogenation barrier and address the chemoselectivity issue. The developed chemistry features operational simplicity, readily available catalyst and good functional group tolerance, and offers a significant basis for further development of new protocols to directly transform or functionalize inert N-heterocycles.

引用

页码：14232 / 14236

页数：5

共 88 条

[51] Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes [J].

Lee, Pin-Sheng ;

Yoshikai, Naohiko .

ORGANIC LETTERS, 2015, 17 (01) :22-25

[52] Manganese-Catalyzed C-H Activation [J].

Liu, Weiping ;

Ackermann, Lutz .

ACS CATALYSIS, 2016, 6 (06) :3743-3752

[53] Recent advances in positional-selective alkenylations: removable guidance for twofold C-H activation [J].

Ma, Wenbo ;

Gandeepan, Parthasarathy ;

Li, Jie ;

Ackermann, Lutz .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07) :1435-1467

[54] A general and efficient aldehyde decarbonylation reaction by using a palladium catalyst [J].

Modak, Atanu ;

Deb, Arghya ;

Patra, Tuhin ;

Rana, Sujoy ;

Maity, Soham ;

Maiti, Debabrata .

CHEMICAL COMMUNICATIONS, 2012, 48 (35) :4253-4255

[55] Fused Indolines by Palladium-Catalyzed Asymmetric C-C Coupling Involving an Unactivated Methylene Group [J].

Nakanishi, Masafumi ;

Katayev, Dmitry ;

Besnard, Celine ;

Kuendig, E. Peter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) :7438-7441

[56] Hydroarylation of Alkynes Catalyzed by Nickel [J].

Nakao, Yoshiaki .

CHEMICAL RECORD, 2011, 11 (05) :242-251

[57] Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes [J].

Narute, Sachin ;

Parnes, Regev ;

Toste, F. Dean ;

Pappo, Doron .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (50) :16553-16560

[58] Catalytic Enantioselective Transformations Involving C-H Bond Cleavage by Transition-Metal Complexes [J].

Newton, Christopher G. ;

Wang, Shou-Guo ;

Oliveira, Caio C. ;

Cramer, Nicolai .

CHEMICAL REVIEWS, 2017, 117 (13) :8908-8976

[59] Total synthesis of (+)-lithospermic acid by asymmetric intramolecular alkylation via catalytic C-H bond activation [J].

O'Malley, SJ ;

Tan, KL ;

Watzke, A ;

Bergman, RG ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13496-13497

[60] Ir(I)-Catalyzed C-H Bond Alkylation of C2-Position of Indole with Alkenes: Selective Synthesis of Linear or Branched 2-Alkylindoles [J].

Pan, Shiguang ;

Ryu, Naoto ;

Shibata, Takanori .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17474-17477

← 1 2 3 4 5 6 7 8 9 →