Visible-light-promoted cross-coupling reaction of hypervalent bis-catecholato silicon compounds with selenosulfonates or thiosulfonates

被引:25
作者
Wang, Fei [1 ]
Wang, Shun-Yi [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
INTRAMOLECULAR HOMOLYTIC SUBSTITUTION; OXIDATION; SELENIUM; ALKYLATION; GENERATION; SILICATES; PENTACOORDINATE; ALKYLSILICATES; SPECIATION; CATALYSIS;
D O I
10.1039/d1qo00085c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under mild metal-free conditions, we successfully developed a visible-light-promoted free radical cross coupling of hypervalent bis-catecholato silicon compounds with selenosulfonates or thiosulfonates and efficiently constructed unsymmetrical 1 degrees-alkyl-alkyl selenide compounds which are difficult to prepare. This protocol uses mild reaction conditions and easily available substrates, has a wide range substrate scope, high yields, and simple operation and no need of expensive photosensitive catalysts. It provides a green and simple method for the preparation of unsymmetrical alkyl-alkyl selenide compounds. At the same time, this strategy is also applicable for the efficient construction of aryl-alkyl selenides, heteroayl-alkyl selenides and aryl-alkyl sulfides.
引用
收藏
页码:1976 / 1982
页数:7
相关论文
共 52 条
[1]   Intramolecular homolytic substitution at selenium:: Synthesis of novel selenium-containing vitamin E analogues [J].
Al-Maharik, N ;
Engman, L ;
Malmström, J ;
Schiesser, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6286-6290
[2]   On the stability of 2-aminoselenophene-3-carboxylates:: potential dual-acting selenium-containing allosteric enhancers of A1 adenosine receptor binding [J].
Aumann, Kylee M. ;
Scammells, Peter J. ;
White, Jonathan M. ;
Schiesser, Carl H. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (08) :1276-1281
[3]   TMSCl-promoted selective oxidation of sulfides to sulfoxides with hydrogen peroxide [J].
Bahrami, Kiumars ;
Khodaei, Mohammad M. ;
Yousefi, Behrooz H. ;
Arabi, Mehdi Sheikh .
TETRAHEDRON LETTERS, 2010, 51 (52) :6939-6941
[4]   Preparation of novel selenapenams and selenacephems by nucleophilic and radical chemistry involving benzyl selenides [J].
Carland, MW ;
Martin, RL ;
Schiesser, CH .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (18) :2612-2618
[5]   Intramolecular homolytic substitution at the sulfur atom: an alternative way to generate phosphorus- and sulfur-centered radicals [J].
Carta, Paola ;
Puljic, Nicolas ;
Robert, Carine ;
Dhimane, Anne-Lise ;
Ollivier, Cyril ;
Fensterbank, Louis ;
Lacote, Emmanuel ;
Malacria, Max .
TETRAHEDRON, 2008, 64 (52) :11865-11875
[6]   Synthesis of Aliphatic Amides through a Photoredox Catalyzed Radical Carbonylation Involving Organosilicates as Alkyl Radical Precursors [J].
Cartier, Alex ;
Levernier, Etienne ;
Dhimane, Anne-Lise ;
Fukuyama, Takahide ;
Ollivier, Cyril ;
Ryu, Ilhyong ;
Fensterbank, Louis .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (11) :2254-2259
[7]   Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis [J].
Cartier, Alex ;
Levernier, Etienne ;
Corce, Vincent ;
Fukuyama, Takahide ;
Dhimane, Anne-Lise ;
Ollivier, Cyril ;
Ryu, Ilhyong ;
Fensterbank, Louis .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) :1789-1793
[8]   Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis [J].
Chen, Wenxin ;
Liu, Zheng ;
Tian, Jiaqi ;
Li, Jin ;
Ma, Jing ;
Cheng, Xu ;
Li, Guigen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (38) :12312-12315
[9]   Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond To Form Two Stereogenic Centers in an Aqueous Medium [J].
Chen, Zhili ;
Hu, Fangli ;
Huang, Shengli ;
Zhao, Zhengxing ;
Mao, Hui ;
Qin, Wenling .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) :8100-8111
[10]   Single-Electron-Transfer Oxidation of Trifluoroborates and Silicates with Organic Reagents: A Comparative Study [J].
Chenneberg, Ludwig ;
Leveque, Christophe ;
Corce, Vincent ;
Baralle, Alexandre ;
Goddard, Jean-Philippe ;
Ollivier, Cyril ;
Fensterbank, Louis .
SYNLETT, 2016, 27 (05) :731-735