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
Synthesis 2009(10): 1732-1738
DOI: 10.1055/s-0029-1216644
DOI: 10.1055/s-0029-1216644
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Catalyst-Free and Base-Free Water-Promoted SNAr Reaction of Heteroaryl Halides with Thiols
Further Information
Received
12 January 2009
Publication Date:
14 April 2009 (online)
Publication History
Publication Date:
14 April 2009 (online)
Abstract
A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products.
Key words
heteroaryl halides - thiophenol - SNAr reaction - water - 2-thiopyridines
-
1a
Ma X.Gang DR. Nat. Prod. Rep. 2004, 21: 752 -
1b
Nayyar A.Jain R. Curr. Med. Chem. 2005, 12: 1873 -
1c
Wishka DG.Graber DR.Kopta LA.Olmsted RA.Friis JM.Hosley JD.Adams WJ.Seest EP.Castle TM.Dolak LA.Keiser BJ.Yagi Y.Jeganathan A.Schlachter ST.Murphy MJ.Cleek GJ.Nugent RA.Poppe SM.Swaney SM.Han F.Watt W.White WL.Poel T.-J.Thomas RC.Voorman RL.Stefanski KJ.Stehle RG.Tarpley WG.Morris J. J. Med. Chem. 1998, 41: 1357 -
1d
Pathak AK.Pathak V.Seitz LE.Suling WJ.Reynolds RC. J. Med. Chem. 2004, 47: 273 - 2
Lowe JA.Qian W.Drozda SE.Volkmann RA.Nason D.Nelson RB.Nolan C.Liston D.Ward K.Faraci S.Verdries K.Seymour P.Majchrzak M.Villalobos A.White WF. J. Med. Chem. 2004, 47: 1575 -
3a
Perrier V.Wallace AC.Kaneko K.Safar J.Prusiner SB.Cohen FE. Proc. Natl. Acad. Sci. U.S.A. 2000, 97: 6073 -
3b
Trankle WG.Kopach ME. Org. Process Res. Dev. 2007, 11: 913 -
4a
Herradura PS.Pendola KA.Guy RK. Org. Lett. 2000, 2: 2019 -
4b
Kwong FY.Buchwald SL. Org. Lett. 2002, 4: 3517 -
4c
Li GY.Zheng G.Noonan AF. J. Org. Chem. 2001, 66: 8677 -
4d
Hickman RJS.Christie BJ.Guy RW.White TJ. Aust. J. Chem. 1985, 38: 899 -
4e
Taniguchi N.Onami T. J. Org. Chem. 2004, 69: 915 -
4f
Adapa RS.Alam MM.Ramu RE. Chem. Lett. 2004, 33: 1614 -
5a
Cheng Y. Tetrahedron 2002, 58: 4931 -
5b
McDonald JW.Le Bleu RE.Quin LD.Bradsher CK. J. Org. Chem. 1961, 26: 4944 -
5c
Tundo P.Anastas P.Black DS.Breen J.Collins T.Memoli S.Miyamoto J.Polyakoff M.Tumas W. Pure Appl. Chem. 2000, 72: 1207 -
6a
Breslow R.Rideout DC. J. Am. Chem. Soc. 1980, 102: 7816 -
6b
Narayan S.Muldoon J.Finn MG.Fokin FV.Kolb HC.Sharpless KB. Angew. Chem. Int. Ed. 2005, 44: 3275 -
6c
Shapiro N.Vigalok A. Angew. Chem. Int. Ed. 2008, 47: 2849 -
6d
Khatik GL.Kumar R.Chakraborti AK. Org. Lett. 2006, 8: 2433 -
6e
Wang Z.Cui YT.Xu ZB.Qu J. J. Org. Chem. 2008, 73: 2270 -
6f
Azizi N.Saisi MR. Org. Lett. 2005, 7: 3649 -
7a
Sreedhar B.Reddy PS.Krishna CSV.Babu PV. Tetrahedron Lett. 2007, 48: 7882 -
7b
Sreedhar B.Reddy PS.Kumar NS. Tetrahedron Lett. 2006, 47: 3055 -
7c
Sreedhar B.Reddy PS.Prakash BV.Ravindra A. Tetrahedron Lett. 2005, 46: 7019 -
9a
Akerlof GC.Oshry HI. J. Am. Chem. Soc. 1950, 72: 2844 -
9b
Miller DJ.Hawthorne SB. J. Chem. Eng. Data 2000, 45: 78 - 10
van der Plas HC. Acc. Chem. Res. 1978, 11: 462
References
Elkington J.; http://www.sustainability.co.uk/sustainability.htm>.