Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2015; 47(07): 969-975
DOI: 10.1055/s-0034-1379972
DOI: 10.1055/s-0034-1379972
paper
Synthesis of β-Trifluoromethylthio- and β-Trifluoromethylseleno-α,β-unsaturated Ketones through Copper-Mediated Trifluoromethylthio(seleno)lation
Authors
Further Information
Publication History
Received: 29 September 2012
Accepted after revision: 11 December 2014
Publication Date:
22 January 2015 (online)
Abstract
An efficient and convenient synthetic methodology has been developed with which to construct β-trifluoromethylthio- and seleno-α,β-unsaturated ketones through copper-mediated trifluoromethylthio(seleno)lation of β-bromo α,β-unsaturated ketones. The corresponding ketone products were isolated in moderate to good yields and were efficiently converted into valuable alcohols.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034–1379972.
- Supporting Information (PDF)
-
References
- 1a Becker A. Inventory of Industrial Fluoro-Biochemicals. Eyrolles; Paris: 1996
- 1b Langlois BR, Billard T, Large S, Roques N. Fluorinated Bio-active Compounds . Fluorine Technology; Cheshire: 1999. paper 24
- 1c Boiko VN. Beilstein J. Org. Chem. 2010; 6: 880
- 2a Tlili A, Billard T. Angew. Chem. Int. Ed. 2013; 52: 6818
- 2b Wang H, Vicic DA. Synlett 2013; 24: 1887
- 2c He W, Weng Z. Prog. Chem. (Chinese) 2013; 25: 1071
- 2d Chu L, Qing F.-L. Acc. Chem. Res. 2014; 47: 1513
- 2e Toulgoat F, Alazet S, Billard T. Eur. J. Org. Chem. 2014; 2415
- 3a Pooput C, Dolbier WR, Médebielle M. J. Org. Chem. 2006; 71: 3564
- 3b Blond G, Billard T, Langlois BR. Tetrahedron Lett. 2001; 42: 2473
- 3c Roques N. J. Fluorine Chem. 2001; 107: 311
- 3d Billard T, Langlois BR. Tetrahedron Lett. 1996; 37: 6865
- 4a Teruo U, Sumi I. Tetrahedron Lett. 1990; 31: 3579
- 4b Umemoto T, Ishihara S. J. Am. Chem. Soc. 1993; 115: 2156
- 4c Kieltsch I, Eisenberger P, Togni A. Angew. Chem. Int. Ed. 2007; 46: 754
- 5a Wakselman C, Tordeux M. J. Org. Chem. 1985; 50: 4047
- 5b Wakselman C, Tordeux M, Clavel J.-L, Langlois B. J. Chem. Soc., Chem. Commun. 1991; 993
- 5c Quiclet-Sire B, Saicic RN, Zard SZ. Tetrahedron Lett. 1996; 37: 9057
- 5d Billard T, Roques N, Langlois BR. J. Org. Chem. 1999; 64: 3813
- 5e Pooput C, Medebielle M, Dolbier WR. Org. Lett. 2004; 6: 301
- 5f Harsányi A, Dorkó É, Csapó Á, Bakó T, Peltz C, Rábai J. J. Fluorine Chem. 2011; 132: 1241
- 6a Teverovskiy G, Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 7312
- 6b Chen C, Xie Y, Chu L, Wang R.-W, Zhang X, Qing F.-L. Angew. Chem. Int. Ed. 2012; 51: 2492
- 6c Zhang C.-P, Vicic DA. J. Am. Chem. Soc. 2012; 134: 183
- 6d Zhang C.-P, Vicic DA. Chem. Asian J. 2012; 7: 1756
- 6e Tran LD, Popov I, Daugulis O. J. Am. Chem. Soc. 2012; 134: 18237
- 6f Yang Y.-D, Azuma A, Tokunaga E, Yamasaki M, Shiro M, Shibata N. J. Am. Chem. Soc. 2013; 135: 8782
Reference Ris Wihthout Link
- 6g Rueping M, Tolstoluzhsky N, Nikolaienko P. Chem. Eur. J. 2013; 19: 14043
- 6h Shao X, Wang X, Yang T, Lu L, Shen Q. Angew. Chem. Int. Ed. 2013; 52: 3457
Reference Ris Wihthout Link
- 6i Hu F, Shao X, Zhu D, Lu L, Shen Q. Angew. Chem. Int. Ed. 2014; 53: 6105
- 6j Danoun G, Bayarmagnai B, Gruenberg MF, Goossen LJ. Chem. Sci. 2014; 5: 1312
- 7a Ferry A, Billard T, Langlois BR, Bacqué E. Angew. Chem. Int. Ed. 2009; 48: 8551
- 7b Yang Y, Jiang X, Qing F.-L. J. Org. Chem. 2012; 77: 7538
- 7c Ferry A, Billard T, Bacqué E, Langlois BR. J. Fluorine Chem. 2012; 134: 160
- 7d Baert F, Colomb J, Billard T. Angew. Chem. Int. Ed. 2012; 51: 10382
- 7e Alazet S, Zimmer L, Billard T. Angew. Chem. Int. Ed. 2013; 52: 10814
- 7f Bootwicha T, Liu X, Pluta R, Atodiresei I, Rueping M. Angew. Chem. Int. Ed. 2013; 52: 12856
- 7g Wang X, Yang T, Cheng X, Shen Q. Angew. Chem. Int. Ed. 2013; 52: 12860
- 7h Pluta R, Nikolaienko P, Rueping M. Angew. Chem. Int. Ed. 2014; 53: 1650
Reference Ris Wihthout Link
- 7i Vinogradova EV, Müller P, Buchwald SL. Angew. Chem. Int. Ed. 2014; 53: 3125
- 7j Xu C, Ma B, Shen Q. Angew. Chem. Int. Ed. 2014; 53: 9316
Reference Ris Wihthout Link
- 8 Piers E, Grierson JR, Lau CK, Nagakura I. Can. J. Chem. 1982; 60: 210
- 9a Byeon SR, Park H, Kim H, Hong J. Org. Lett. 2011; 13: 5816
- 9b Korenaga T, Maenishi R, Hayashi K, Sakai T. Adv. Synth. Catal. 2010; 352: 3247
- 9c Jun C.-H, Moon CW, Kim Y.-M, Lee H, Lee JH. Tetrahedron Lett. 2002; 43: 4233
- 10a Weng Z, He W, Chen C, Lee R, Tan D, Lai Z, Kong D, Yuan Y, Huang K.-W. Angew. Chem. Int. Ed. 2013; 52: 1548
- 10b Kong D, Jiang Z, Xin S, Bai Z, Yuan Y, Weng Z. Tetrahedron 2013; 69: 6046
- 10c Tan J, Zhang G, Ou Y, Yuan Y, Weng Z. Chin. J. Chem. 2013; 31: 921
- 11a Chen C, Ouyang L, Lin Q, Liu Y, Hou C, Yuan Y, Weng Z. Chem. Eur. J. 2014; 20: 657
- 11b Chen C, Hou C, Wang Y, Hor TS. A, Weng Z. Org. Lett. 2013; 16: 524
- 12 Zhu P, He X, Chen X, You Y, Yuan Y, Weng Z. Tetrahedron 2014; 70: 672
- 13 Dang L, Lin Z, Marder TB. Organometallics 2008; 27: 4443
- 14a Piers E, Nagakura I. J. Org. Chem. 1975; 40: 2694
- 14b Piers E, Cheng KF, Nagakura I. Can. J. Chem. 1982; 60: 1256
- 15 Kerr WJ, Pearson CM, Thurston GJ. Org. Biomol. Chem. 2006; 4: 47
- 16 Armerego WL. F, Chai CL. L. Purification of Laboratory Chemicals . 6th ed. Elsevier; Amsterdam: 2009