Copper-Catalyzed Oxidative Trifunctionalization of Olefins: An Access to Functionalized β-Keto Thiosulfones

被引：55
作者：
Huang, Shuai [1 ]
Thirupathi, Nuligonda [1 ]
Tung, Chen-Ho [1 ]
Xu, Zhenghu [1 ,2 ]
机构：
[1] Shandong Univ, Sch Chem & Chem Engn, Minist Educ, Key Lab Colloid & Interface Chem, 27 South Shanda Rd, Jinan 250100, Shandong, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期
关键词：
SULFENYLATED CARBONYL-COMPOUNDS; ALPHA-OXYGENATED KETONES; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; AEROBIC OXYSULFONYLATION; MOLECULAR-OXYGEN; BOND FORMATION; SULFUR BOND; ALKENES; EFFICIENT;
D O I：
10.1021/acs.joc.8b01161
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aerobic oxidative trifunctionalization of olefins for the synthesis of functionalized beta-keto thiosulfones has been described. The transformation proceeds through molecular oxygen activation under copper catalysis and forms the two new C-S bonds in a single operation using mild conditions. A novel Cu-catalyzed sulfonyl radical addition/oxidation/funtionalization relay mechanism was proposed for the discovered reaction.
引用
收藏
页码：9449 / 9455
页数：7
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[51]   Copper(II) Triflate-Catalyzed Aerobic Oxidative C-H Functionalization of Glycine Derivatives with Olefins and Organoboranes [J].
Xie, Zhiyu ;
Jia, Jiong ;
Liu, Xigong ;
Liu, Lei .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (06) :919-925
[52]   Stevens rearrangement of thioethers with arynes: a facile access to multi-substituted β-keto thioethers [J].
Xu, Xiao-Bo ;
Lin, Zi-Hua ;
Liu, Yuyin ;
Guo, Jian ;
He, Yun .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (13) :2716-2720
[53]   Rongalite® mediated highly regioselective aerobic hydroxysulfenylation of styrenes with disulfides: a convenient approach to β-hydroxy sulfides [J].
Yadav, Vinod K. ;
Srivastava, Vishnu P. ;
Yadav, Lal Dhar S. .
TETRAHEDRON LETTERS, 2015, 56 (22) :2892-2895
[54]   Visible-light initiated direct oxysulfonylation of alkenes with sulfinic acids leading to β-ketosulfones [J].
Yang, Daoshan ;
Huang, Ben ;
Wei, Wei ;
Li, Jin ;
Lin, Gu ;
Liu, Yaru ;
Ding, Jiehua ;
Sun, Pengfei ;
Wang, Hua .
GREEN CHEMISTRY, 2016, 18 (20) :5630-5634
[55]   Palladium(II)-Catalyzed Oxidative Difunctionalization of Alkenes: Bond Forming at a High-Valent Palladium Center [J].
Yin, Guoyin ;
Mu, Xin ;
Liu, Guosheng .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (11) :2413-2423
[56]   Copper-catalyzed carbene insertion into the sulfur-sulfur bond of benzenesulfonothioate [J].
Yuan, Hairui ;
Nuligonda, Thirupathi ;
Gao, Hongyin ;
Tung, Chen-Ho ;
Xu, Zhenghu .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08) :1371-1374
[57]   DDQ-Mediated Three-Component Dioxygenation of Alkenes [J].
Zhang, Tian-Shu ;
Xiong, Yan-Jie ;
Hao, Wen-Juan ;
Zhu, Xiao-Tong ;
Wang, Shu-Liang ;
Li, Guigen ;
Tu, Shu-Jiang ;
Jiang, Bo .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :9350-9355
[58]   Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes [J].
Zhao, Wanxiang ;
Montgomery, John .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (31) :9763-9766
[59]   Air Oxidative Radical Hydroxysulfurization of Styrenes Leading to β-Hydroxysulfides [J].
Zhou, Shao-Fang ;
Pan, Xiangqiang ;
Zhou, Zhi-Hao ;
Shoberu, Adedamola ;
Zou, Jian-Ping .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (07) :3682-3687
[60]   Copper-Catalyzed Synthesis of α-Thioaryl Carbonyl Compounds Through S-S and C-C Bond Cleavage [J].
Zou, Liang-Hua ;
Priebbenow, Daniel L. ;
Wang, Long ;
Mottweiler, Jakob ;
Bolm, Carsten .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) :2558-2563
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