Sulfonamides as new hydrogen atom transfer (HAT) catalysts for photoredox allylic and benzylic C-H arylations

被引:104
作者
Tanaka, Hirotaka [1 ]
Sakai, Kentaro [1 ]
Kawamura, Atsushi [1 ]
Oisaki, Kounosuke [1 ]
Kanai, Motomu [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
关键词
BOND FUNCTIONALIZATION; ALKYLATION; ACTIVATION; ELECTRON; RADICALS;
D O I
10.1039/c7cc09457d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalytic amount of a sterically and electronically tuned diaryl-sulfonamide promoted allylic and benzylic C-H arylations in cooperation with a visible light photoredox catalyst. This is the first example of the catalytic use of a sulfonamidyl radical to promote the hydrogen atom transfer process.
引用
收藏
页码:3215 / 3218
页数:4
相关论文
共 38 条
[21]   Oxidative Coupling between Two Hydrocarbons: An Update of Recent C-H Functionalizations [J].
Liu, Chao ;
Yuan, Jiwen ;
Gao, Meng ;
Tang, Shan ;
Li, Wu ;
Shi, Renyi ;
Lei, Aiwen .
CHEMICAL REVIEWS, 2015, 115 (22) :12138-12204
[22]   Aerobic Oxidation of Benzylic sp3 C-H Bonds through Cooperative Visible-Light Photoredox Catalysis of N-Hydroxyimide and Dicyanopyrazine [J].
Liu, Xinfei ;
Lin, Lu ;
Ye, Xinyi ;
Tan, Choon-Hong ;
Jiang, Zhiyong .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) :422-425
[23]   Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds [J].
Loh, Yong Yao ;
Nagao, Kazunori ;
Hoover, Andrew J. ;
Hesk, David ;
Rivera, Nelo R. ;
Colletti, Steven L. ;
Davies, Ian W. ;
MacMillan, David W. C. .
SCIENCE, 2017, 358 (6367) :1182-+
[24]   Visible-Light-Promoted Activation of Unactivated C(sp3)-H Bonds and Their Selective Trifluoromethylthiolation [J].
Mukherjee, Satobhisha ;
Maji, Biplab ;
Tlahuext-Aca, Adrian ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (50) :16200-16203
[25]   A General Strategy for Organocatalytic Activation of C-H Bonds via Photoredox Catalysis: Direct Arylation of Benzylic Ethers [J].
Qvortrup, Katrine ;
Rankic, Danica A. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (02) :626-629
[26]   Radical Stability as a Guideline in C-H Amination Reactions [J].
Sakic, Davor ;
Zipse, Hendrik .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (24) :3983-3991
[27]   Photoredox Catalysis in Organic Chemistry [J].
Shaw, Megan H. ;
Twilton, Jack ;
MacMillan, David W. C. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6898-6926
[28]   Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles [J].
Shaw, Megan H. ;
Shurtleff, Valerie W. ;
Terrett, Jack A. ;
Cuthbertson, James D. ;
MacMillan, David W. C. .
SCIENCE, 2016, 352 (6291) :1304-1308
[29]   Applications of Nonenzymatic Catalysts to the Alteration of Natural Products [J].
Shugrue, Christopher R. ;
Miller, Scott J. .
CHEMICAL REVIEWS, 2017, 117 (18) :11894-11951
[30]   Photocatalyst size controls electron and energy transfer: selectable E/Z isomer synthesis via C-F alkenylation [J].
Singh, A. ;
Fennell, C. J. ;
Weaver, J. D. .
CHEMICAL SCIENCE, 2016, 7 (11) :6796-6802