Metal-Free Visible-Light-Mediated Oxidative Cross-Coupling of Thiols with P(O)H Compounds Using Air as the Oxidant

被引:134
作者
Sun, Jian-Guo [1 ]
Yang, Hua [1 ]
Li, Ping [1 ]
Zhang, Bo [1 ]
机构
[1] China Pharmaceut Univ, State Key Lab Nat Med, 24 Tongjia Xiang, Nanjing 210009, Jiangsu, Peoples R China
关键词
SECONDARY PHOSPHINE OXIDES; C-H ARYLATION; PHOTOREDOX CATALYSIS; SINGLET OXYGEN; PROMOTED SYNTHESIS; NICKEL CATALYSIS; ARYL; PHOSPHONATES; THIOPHOSPHATES; AMINES;
D O I
10.1021/acs.orglett.6b02563
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Visible light along with 5 mol % of rose bengal, catalyzes the direct S-P(O) coupling between thiols and P(O) H compounds in the presence of air as the green oxidant. The, protocol is operationally simple and amenable to gram-scale synthesis. A variety of S-P(O) coupling products can be readily. prepared in moderate to excellent yields. The reaction features good functional-group tolerance, operational simplicity, and excellent practicality.
引用
收藏
页码:5114 / 5117
页数:4
相关论文
共 75 条
[1]   N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].
Allen, Laura J. ;
Cabrera, Pablo J. ;
Lee, Melissa ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) :5607-5610
[2]   Rhodium-catalyzed thiophosphinylation and phosphinylation reactions of disulfides and diselenides [J].
Arisawa, M ;
Ono, T ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2005, 46 (34) :5669-5671
[3]   STUDIES ON PHOSPHORYLATION .3. FURTHER OBSERVATIONS ON THE REACTION OF PHOSPHITES WITH POLYHALOGEN COMPOUNDS IN PRESENCE OF BASES AND ITS APPLICATION TO THE PHOSPHORYLATION OF ALCOHOLS [J].
ATHERTON, FR ;
TODD, AR .
JOURNAL OF THE CHEMICAL SOCIETY, 1947, (MAY) :674-678
[4]   Reactions of (RP)- and (SP)-tert-butylphenylphosphinobromidates and tert-butylphenylthionophosphinochloridates with heteroatom nucleophiles;: preparation of P-chiral binol phosphinates and related compounds [J].
Au-Yeung, TL ;
Chan, KY ;
Chan, WK ;
Haynes, RK ;
Williams, ID ;
Yeung, LL .
TETRAHEDRON LETTERS, 2001, 42 (03) :453-456
[5]   Copper-catalyzed reductive coupling of aryl sulfonyl chlorides with H-phosphonates leading to S-aryl phosphorothioates [J].
Bai, Jie ;
Cui, Xiuling ;
Wang, Hui ;
Wu, Yangjie .
CHEMICAL COMMUNICATIONS, 2014, 50 (64) :8860-8863
[6]   Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis [J].
Beatty, Joel W. ;
Stephenson, Corey R. J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1474-1484
[7]   DCDMH-promoted synthesis of thiophosphates by coupling of H-phosphonates with thiols [J].
Bi, Xiaojing ;
Li, Junchen ;
Meng, Fanhua ;
Wang, Hongmei ;
Xiao, Junhua .
TETRAHEDRON, 2016, 72 (05) :706-711
[8]   Visible light C-H amidation of heteroarenes with benzoyl azides [J].
Brachet, E. ;
Ghosh, T. ;
Ghosh, I. ;
Koenig, B. .
CHEMICAL SCIENCE, 2015, 6 (02) :987-992
[9]   Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen [J].
Carreño, MC ;
González-López, M ;
Urbano, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) :2737-2741
[10]   Generation of phosphorus-centered radicals via homolytic substitution at sulfur [J].
Carta, Paola ;
Puljic, Nicolas ;
Robert, Carine ;
Dhimane, Anne-Lise ;
Fensterbank, Louis ;
Lacote, Emmanuel ;
Malacria, Max .
ORGANIC LETTERS, 2007, 9 (06) :1061-1063