Light-Mediated Asymmetric Aliphatic C-H Alkylation with Hydrogen Atom Transfer Catalyst and Chiral Phosphoric Acid

被引:65
作者
Dai, Zhen-Yao [1 ]
Nong, Zhong-Sheng [1 ]
Wang, Pu-Sheng [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
关键词
C-H functionalization; asymmetric photocatalysis; hydrogen atom transfer; enantioselective protonation; chiral phosphoric acid; C(SP(3))-H FUNCTIONALIZATION; DIRECT ARYLATION; BONDS; ACTIVATION; 1,1'-SPIROBIINDANE-7,7'-DIOL; SELECTIVITY;
D O I
10.1021/acscatal.0c00610
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In the presence of tetrabutylammonium decatungstate and chiral Spiro phosphoric acid, a light-mediated asymmetric C-H functionalization of unactivated hydrocarbons with exocyclic enones has been established. A wide range of cycloalkanes, benzylic, and allylic hydrocarbons are tolerated. This protocol proceeds via a hydrogen atom transfer/radical addition/hydrogen abstraction/enantioselective protonation relay process.
引用
收藏
页码:4786 / 4790
页数:5
相关论文
共 73 条
[1]   1,1′-spirobiindane-7,7′-diol:: a novel, C2-symmetric chiral ligand [J].
Birman, VB ;
Rheingold, AL ;
Lam, KC .
TETRAHEDRON-ASYMMETRY, 1999, 10 (01) :125-131
[2]   Bond dissociation energies of organic molecules [J].
Blanksby, SJ ;
Ellison, GB .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :255-263
[3]   Decatungstate Photocatalyzed Acylations and Alkylations in Flow via Hydrogen Atom Transfer [J].
Bonassi, Filippo ;
Ravelli, Davide ;
Protti, Stefano ;
Fagnoni, Maurizio .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) :3687-3695
[4]   Light-Driven Single-Electron Transfer Processes as an Enabling Principle in Sulfur and Selenium Multicatalysis [J].
Breder, Alexander ;
Depken, Christian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (48) :17130-17147
[5]   Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis [J].
Capaldo, Luca ;
Ravelli, Davide .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) :2056-2071
[6]   Enantioselective benzylic C-H arylation via photoredox and nickel dual catalysis [J].
Cheng, Xiaokai ;
Lu, Huangzhe ;
Lu, Zhan .
NATURE COMMUNICATIONS, 2019, 10 (1)
[7]   A Bronsted acid catalyst for the enantioselective protonation reaction [J].
Cheon, Cheol Hong ;
Yamamoto, Hisashi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9246-+
[8]   Catalytic alkylation of remote C-H bonds enabled by proton-coupled electron transfer [J].
Choi, Gilbert J. ;
Zhu, Qilei ;
Miller, David C. ;
Gu, Carol J. ;
Knowles, Robert R. .
NATURE, 2016, 539 (7628) :268-271
[9]   Amide-directed photoredox-catalysed C-C bond formation at unactivated sp3 C-H bonds [J].
Chu, John C. K. ;
Rovis, Tomislav .
NATURE, 2016, 539 (7628) :272-275
[10]   Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization [J].
Coric, Ilija ;
Mueller, Steffen ;
List, Benjamin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) :17370-17373