Synthesis of Monofluoromethyl Selenoethers of Aryl and Alkyl from Organoselenocyanate via One-Pot Reaction

被引：23

作者：

Cao, Yuan ^{[1
]}

Jiang, Lvqi ^{[1
]}

Yi, Wenbin ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 18期

基金：

中国国家自然科学基金;

关键词：

First monofluoromethylselenolation; Aryl; Alkyl; Late-stage monofluoromethylselenolation; CATALYZED TRIFLUOROMETHYLSELENOLATION; ORGANIC SELENOCYANATES; O-DIFLUOROMETHYLATION; FLUORINE; TRIFLUOROMETHYLTHIOLATION; ETHERS; CONVENIENT; PERFLUOROALKYLTHIOLATION; DIFLUOROMETHYLTHIOLATION; THIOETHERS;

D O I：

10.1002/adsc.201900480

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first practical and feasible approach for the monofluoromethylselenolation of aryl and alkyl halides via one-pot multistep synthesis using KSeCN and ICFH2 is described. Good yields and broad functional group compatibility were obtained. The successful preparation of monofluoromethylselenolated drug-like compounds good practicability of this method. This protocol offered a number of new monofluoromethyl selenoethers, which would accelerate the use of such compounds in the areas of life science.

引用

页码：4360 / 4368

页数：9

共 66 条

[21] Benzyltrifluoromethyl (or Fluoroalkyl) Selenide: Reagent for Electrophilic Trifluoromethyl (or Fluoroalkyl) Selenolation [J].

Glenadel, Quentin ;

Ismalaj, Ermal ;

Billard, Thierry .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18) :8268-8275

[22] The many roles for fluorine in medicinal chemistry [J].

Hagmann, William K. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369

[23] Nickel-Catalyzed Trifluoromethylselenolation of Aryl Halides Using the Readily Available [Me4N][SeCF3] Salt [J].

Han, Jia-Bin ;

Dong, Tao ;

Vicic, David A. ;

Zhang, Cheng-Pan .

ORGANIC LETTERS, 2017, 19 (14) :3919-3922

[24] A Metal-Free Diverse Synthesis of Difluoromethylthioethers and Difluorobis(arylthio)methanes from RSX (X = SR, CI, SO2Ph) and TMSCF2H [J].

Han, Jia-Bin ;

Qin, Hua-Li ;

Ye, Su-Hong ;

Zhu, Lei ;

Zhang, Cheng-Pan .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06) :2506-2512

[25] A SURVEY OF HAMMETT SUBSTITUENT CONSTANTS AND RESONANCE AND FIELD PARAMETERS [J].

HANSCH, C ;

LEO, A ;

TAFT, RW .

CHEMICAL REVIEWS, 1991, 91 (02) :165-195

[26]

Hansch C., 1979, Substituent constants for correlation analysis in chemistry and biology

[27] Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H [J].

Howard, Joseph L. ;

Schotten, Christiane ;

Alston, Stephen T. ;

Browne, Duncan L. .

CHEMICAL COMMUNICATIONS, 2016, 52 (54) :8448-8451

[28] Selective difluoromethylation and monofluoromethylation reactions [J].

Hu, Jinbo ;

Zhang, Wei ;

Wang, Fei .

CHEMICAL COMMUNICATIONS, 2009, (48) :7465-7478

[29] Direct Trifluoromethylthiolation and Perfluoroalkylthiolation of C(sp2)-H Bonds with CF3SO2Na and RfSO2Na [J].

Jiang, Lvqi ;

Qian, Jinlong ;

Yi, Wenbin ;

Lu, Guoping ;

Cai, Chun ;

Zhang, Wei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) :14965-14969

[30] Versatile application of trifluoromethyl triflate [J].

Kolomeitsev, Alexander A. ;

Vorobyev, Mikhail ;

Gillandt, Hartmut .

TETRAHEDRON LETTERS, 2008, 49 (03) :449-454

← 1 2 3 4 5 6 7 →