Photocatalytic C-C Bond Cleavage and Amination of Cycloalkanols by Cerium(III) Chloride Complex

被引：289

作者：

Guo, Jing-Jing ^{[1
]}

Hu, Anhua ^{[1
]}

Chen, Yilin ^{[1
]}

Sun, Jianfeng ^{[1
]}

Tang, Haoming ^{[1
]}

Zuo, Zhiwei ^{[1
]}

机构：

[1] Shanghai Tech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 49期

关键词：

alcohols; amination; C-C bond cleavage; cerium; photochemistry; ORGANIC-COMPOUNDS; OXIDATIVE CLEAVAGE; CARBON; ACTIVATION; ALCOHOLS; ELECTROPHILES; CONSTRUCTION; CYANATION; COUPLINGS; RADICALS;

D O I：

10.1002/anie.201609035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general strategy for the cleavage and amination of C-C bonds of cycloalkanols has been achieved through visible-light-induced photoredox catalysis utilizing a cerium(III) chloride complex. This operationally simple methodology has been successfully applied to a wide array of unstrained cyclic alcohols, and represents the first example of catalytic C-C bond cleavage and functionalization of unstrained secondary cycloalkanols.

引用

页码：15319 / 15322

页数：4

共 49 条

[1] Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].

Chen, Feng ;

Wang, Teng ;

Jiao, Ning .

CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661

[2] Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway [J].

Creutz, Sidney E. ;

Lotito, Kenneth J. ;

Fu, Gregory C. ;

Peters, Jonas C. .

SCIENCE, 2012, 338 (6107) :647-651

[3] Enantioselective Rh-Catalyzed Carboacylation of C=N Bonds via C-C Activation of Benzocyclobutenones [J].

Deng, Lin ;

Xu, Tao ;

Lo, Hongbo ;

Done, Guangbin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :369-374

[4]

Dong G, 2014, TOP CURR CHEM, V346, P1, DOI 10.1007/978-3-642-55055-3

[5] Phosphors for Solid-State White Lighting [J].

George, Nathan C. ;

Denault, Kristin A. ;

Seshadri, Ram .

ANNUAL REVIEW OF MATERIALS RESEARCH, VOL 43, 2013, 43 :481-501

[6] Selectivity in the chemistry of oxygen-centered radicals - The formation of carbon-oxygen bonds [J].

Hartung, J ;

Gottwald, T ;

Spehar, K .

SYNTHESIS-STUTTGART, 2002, (11) :1469-1498

[7] CERIUM(IV) AMMONIUM NITRATE-CHARCOAL SYSTEM - AN EFFECTIVE CATALYST FOR THE AIR OXIDATION OF BENZYL ALCOHOLS AND ACYLOINS [J].

HATANAKA, Y ;

IMAMOTO, T ;

YOKOYAMA, M .

TETRAHEDRON LETTERS, 1983, 24 (23) :2399-2400

[8] LUMINESCENCE SPECTRA OF A SERIES OF CERIUM(III) HALIDES AND ORGANOMETALLICS - PROBES OF BONDING PROPERTIES USING 4F-5D EXCITED-STATES [J].

HAZIN, PN ;

BRUNO, JW ;

BRITTAIN, HG .

ORGANOMETALLICS, 1987, 6 (05) :913-918

[9] Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature [J].

Hien-Quang Do ;

Bachman, Shoshana ;

Bissember, Alex C. ;

Peters, Jonas C. ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (05) :2162-2167

[10] Talampanel [J].

Howes, John F. ;

Bell, Cynthia .

NEUROTHERAPEUTICS, 2007, 4 (01) :126-129

← 1 2 3 4 5 →