Nickel-Catalyzed Defluorinative Reductive Cross-Coupling Reaction of gem-Difluoroalkenes with Thiosulfonate or Selenium Sulfonate

被引：71
作者：
Li, Jian [1 ,2 ]
Rao, Weidong [3 ]
Wang, Shun-Yi [1 ,2 ]
Ji, Shun-Jun [1 ,2 ]
机构：
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China
[3] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Jiangsu, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期
基金：
中国国家自然科学基金;
关键词：
REGIOSELECTIVE SULFENYLATION; METAL-FREE; INDOLES; FLUOROALKENES; DISULFIDES; BORYLATION; REAGENTS; ALKYL;
D O I：
10.1021/acs.joc.9b01387
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A nickel-catalyzed defluorinative reductive cross-coupling of gem-difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high E-selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.
引用
收藏
页码：11542 / 11552
页数：11
相关论文
共 62 条
[1]   Manganese-catalyzed synthesis of monofluoroalkenes via C-H activation and C-F cleavage [J].
Cai, Sai-Hu ;
Ye, Lu ;
Wang, Ding-Xing ;
Wang, Yi-Qiu ;
Lai, Lin-Jie ;
Zhu, Chuan ;
Feng, Chao ;
Loh, Teck-Peng .
CHEMICAL COMMUNICATIONS, 2017, 53 (62) :8731-8734
[2]   Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles [J].
Chen, JW ;
Law, CCW ;
Lam, JWY ;
Dong, YP ;
Lo, SMF ;
Williams, ID ;
Zhu, DB ;
Tang, BZ .
CHEMISTRY OF MATERIALS, 2003, 15 (07) :1535-1546
[3]   N-Heterocyclic carbene-catalyzed stereoselective construction of olefinic carbon-sulfur bonds via cross-coupling reaction of gem-difluoroalkenes and thiols [J].
Cong, Zi-Song ;
Li, Yang-Guo ;
Chen, Lei ;
Xing, Fen ;
Du, Guang-Fen ;
Gu, Cheng-Zhi ;
He, Lin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (18) :3863-3868
[4]   Sterically Controlled Cu-Catalyzed or Transition-Metal-Free Cross-Coupling of gem-Difluoroalkenes with Tertiary, Secondary, and Primary Alkyl Grignard Reagents [J].
Dai, Wenpeng ;
Shi, Hongyan ;
Zhao, Xianghu ;
Cao, Song .
ORGANIC LETTERS, 2016, 18 (17) :4284-4287
[5]   Diastereomeric fluoroolefins as peptide bond mimics prepared by asymmetric reductive amination of α-fluoroenones [J].
Dutheuil, Guillaume ;
Couve-Bonnaire, Samuel ;
Pannecoucke, Xavier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (08) :1290-1292
[6]   Cross-Electrophile Coupling: Principles of Reactivity and Selectivity [J].
Everson, Daniel A. ;
Weix, Daniel J. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11) :4793-4798
[7]   Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides [J].
Fang, Yi ;
Rogge, Torben ;
Ackermann, Lutz ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
NATURE COMMUNICATIONS, 2018, 9
[8]   Pinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement Strategies [J].
Fuchibe, Kohei ;
Morikawa, Toshiyuki ;
Shigeno, Kento ;
Fujita, Takeshi ;
Ichikawa, Junji .
ORGANIC LETTERS, 2015, 17 (05) :1126-1129
[9]   Glycosyl phenylthiosulfonates (Glyco-PTS): novel reagents for glycoprotein synthesis [J].
Gamblin, DP ;
Garnier, P ;
Ward, SJ ;
Oldham, NJ ;
Fairbanks, AJ ;
Davis, BG .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (21) :3642-3644
[10]   AgF-Mediated Fluorinative Cross-Coupling of Two Olefins: Facile Access to α-CF3 Alkenes and β-CF3 Ketones [J].
Gao, Bing ;
Zhao, Yanchuan ;
Hu, Jinbo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) :638-642
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