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
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
收藏
页码:15319 / 15322
页数:4
相关论文
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