Rh(III)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C-H activation

被引：99

作者：

Shi, Zhuangzhi ^{[1
]}

Boultadakis-Arapinis, Melissa ^{[1
]}

Koester, Dennis C. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 20期

基金：

欧洲研究理事会;

关键词：

AROMATIC IMINES; EFFICIENT SYNTHESIS; BOND ACTIVATION; ANNULATION; INDOLIZIDINE; HYDROARYLATION; AGONIST; ALKYNES; ACID;

D O I：

10.1039/c4cc00029c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Biologically interesting fused oligocyclic lactams have been prepared via an intramolecular redox-neutral cyclization process. By the proper choice of the substrates with a wide variety of tethered olefins, the less favored C-H bond can be activated and functionalized. This C-H activation proceeds under mild conditions, obviates the need for external oxidants, and displays a broad scope with respect to the substituents.

引用

页码：2650 / 2652

页数：3

共 45 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation [J].

Ahrendt, KA ;

Bergman, RG ;

Ellman, JA .

ORGANIC LETTERS, 2003, 5 (08) :1301-1303

[3] Short, enantioselective total synthesis of okaramine N [J].

Baran, PS ;

Guerrero, CA ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) :5628-5629

[4] A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization [J].

Baran, PS ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7904-7905

[5] Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy [J].

Beck, Elizabeth M. ;

Hatley, Richard ;

Gaunt, Matthew J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3004-3007

[6] Rh(III)-catalyzed C-H activation/cycloaddition of benzamides and methylenecyclopropanes: divergence in ring formation [J].

Cui, Sunliang ;

Zhang, Yan ;

Wu, Qifan .

CHEMICAL SCIENCE, 2013, 4 (09) :3421-3426

[7] C-H Functionalization in organic synthesis [J].

Davies, Huw M. L. ;

Du Bois, Justin ;

Yu, Jin-Quan .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1855-1856

[8] Rhodium(III)-Catalyzed Intramolecular Hydroarylation, Amidoarylation, and Heck-type Reaction: Three Distinct Pathways Determined by an Amide Directing Group [J].

Davis, Tyler A. ;

Hyster, Todd K. ;

Rovis, Tomislav .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14181-14185

[9]

De Leon Andrew, 2006, Proc (Bayl Univ Med Cent), V19, P413

[10] Cobalt-Catalyzed Intramolecular Olefin Hydroarylation Leading to Dihydropyrroloindoles and Tetrahydropyridoindoles [J].

Ding, Zhenhua ;

Yoshikai, Naohiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) :8574-8578

← 1 2 3 4 5 →