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 2008(15): 2327-2332
DOI: 10.1055/s-2008-1078598
DOI: 10.1055/s-2008-1078598
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA Green Reagent for the Iodination of Phenols
Further Information
Received
8 February 2008
Publication Date:
17 July 2008 (online)
Publication History
Publication Date:
17 July 2008 (online)
Abstract
A new reagent (I2/NaNO2) for the iodination of the aromatic ring of phenols has been discovered. The reaction proceeds at room temperature in 1.5-6 hours. In the presence of this reagent, iodinated compounds are regioselectively formed in significant yields from the corresponding substrates.
Key words
iodination - phenols - sodium nitrite - Lewis acid - eco-friendly
- 1
Firouzabadi H.Iranpoor N.Shiri M. Tetrahedron Lett. 2003, 44: 8781 - 2
Radner F. J. Org. Chem. 1988, 53: 3548 - 3a
Hajipour AR.Arbabian M.Ruoho AE. J. Org. Chem. 2002, 67: 8622 - 3b
Inoguchi Y.Okui S.Mochida K.Itai A. Bull. Chem. Soc. Jpn. 1985, 58: 974 - 3c
Al-Lohedan HA. Orient. J. Chem. 1990, 6: 251 ; Chem. Abstr. 1991, 114: 228448 - 3d
Gaude D.Gellon G.Le Goaller R.Pierre J.-L. Can J. Chem. 1989, 67: 104 - 3e
Boothe R.Dial C.Conaway R.Pagnl RM.Kabalka GW. Tetrahedron Lett. 1986, 27: 2207 - 3f
Horiuchi CA.Satoh JY. Bull. Chem. Soc. Jpn. 1984, 57: 2691 - 3g
Jereb M.Zupan M.Stavber S. Chem. Commun. 2004, 2614 - 3h
Krishna Mohan KVV.Narender N.Kulkarni SJ. Tetrahedron Lett. 2004, 45: 8015 - 3i
Das B.Krishnaiah M.Venkateswarlu K.Saidi Reddy V. Tetrahedron Lett. 2007, 48: 81 - 3j
Johnson R.Meijer A.Ellervik U. Tetrahedron 2005, 61: 11657 - 3k
Orito K.Hatakeyama T.Takeo M.Suginome H. Synthesis 1995, 1273 - 3l
Wing-Wah S. Tetrahedron Lett. 1993, 34: 6223 - 3m
Blackmore IJ.Boa AN.Murray EJ.Dennia M.Woodward S. Tetrahedron Lett. 1999, 40: 6671 - 3n
Holzapfel CW.Bradley D.Williams G. Tetrahedron 1995, 51: 8555 - 3o
Kitagawa H.Shibata T.Matsuo J.Mukaiyama T. Bull. Chem. Soc. Jpn. 2002, 75: 339 - 4
McNamara CA.Dixon MJ.Bradley M. Chem. Rev. 2002, 102: 3275 - 5a
Chaikovski VK.Kharlova TS.Filimonov VD.Saryucheva TA. Synthesis 1999, 748 - 5b
Meruchev EB. Synthesis 1998, 923 - 5c
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 - 6
Snieckus V. Chem. Rev. 1990, 90: 879 - 7
Konakahara T,Kato A,Kurasaki H, andSakai N. inventors; Jpn. Kokai Tokkyo Koho JP 2006321724. ; Chem. Abstr. , 146, 728 - 8a
Kajigaeshi S.Kakinami T.Yamasaki H.Fujisaki S.Kondo M.Okamoto T. Chem. Lett. 1987, 16: 2109 - 8b
Abdol Reza H.Hadi A. J. Chem. Res., Synop. 2004, 294 - 9a
Delvi RR.Sawant SG.Terse PS. Vet. Res. Commun. 1990, 14: 411 - 9b
Larsson SC.Wolk A. Int. J. Cancer. 2006, 119: 2657 - 9c
Björne H.Petersson J.Phillipson M.Weitzberg E.Holm L.Lundberg JO. J. Clin. Invest. 2004, 113: 106 - 9d
Finan A.Keenan P.Donovan F.Murphy J. Brit. Med. J. 1998, 317: 1138 - 10
Hodgson HH. Chem. Rev. 1947, 40: 251 - 11
Jong GL.Hee TC. Tetrahedron Lett. 1992, 33: 3167 - 12
Tandon PK.Baboo R.Singh AK. .Purwar M. Appl. Organomet. Chem. 2005, 19: 1079 - 13
Pohnert G. J. Prakt. Chem. 2000, 342: 731 - 14a
Cotton FA.Wilkinson G.Murillo CA.Bochmann M. Advanced Inorganic Chemistry 6th ed.: Wiley; New York: 1999. - 14b
Hippler H.Luther K.Teitelbaum H.Troe J. Int. J. Chem. Kinet. 1977, 9: 917 - 14c
Bauer H.Rosenthal SM. J. Am. Chem. Soc. 1944, 66: 611 - 15a
Bosch E.Kochi JK. J. Org. Chem. 1994, 59: 5573 - 15b
Uemura S.Onoe A.Okano M. Bull. Chem. Soc. Jpn. 1974, 47: 147 - 15c
Sugita T.Idei M.Ishibashi Y.Takegami Y. Chem. Lett. 1982, 1481 - 16a
Whitmore FC.Hanson ER. Org. Synth. Coll. Vol. 1 Wiley; New York: 1956. p.326 - 16b
Edgar KJ.Falling SN. J. Org. Chem. 1990, 55: 5287 - 16c
Georgiades SN.Clardy J. Org. Lett. 2006, 8: 4251 - 16d
King G.McCombie H. Proc. Chem. Soc. 1913, 29: 8 - 16e
Cambie RC.Larsen DS.Rutledge PS.Woodgate PD. Aust. J. Chem. 1997, 50: 767 - 16f
Bates CG.Saejueng P.Murphy JM.Venkataraman D. Org. Lett. 2002, 4: 4727 - 16g
Woo LWL.Bubert C.Sutcliffe OB.Smith A.Surinder KC.Mahon MF.Purohit A.Reed MJ.Potter BVL. J. Med. Chem. 2007, 50: 3540 - 16h
Bordeianu CV. Arch. Pharm. (Weinheim, Ger.) 1934, 272: 8 - 16i
Schoutissen HAJ. J. Am. Chem. Soc. 1933, 55: 4535 - 16j
Hodgen HH.Moore FH. J. Chem. Soc. 1925, 2260 - 16k
Ohmichi M.Pang L.Ribon V.Gazit A.Levitzki A. Biochemistry 1993, 32: 4650 - 16l
Castella M.Lopez-Calahorra F.Velasco D.Finkelmann H. Liq. Cryst. 2002, 29: 559 - 16m
de Kruif CG.Smit EJ.Govers HAJ. J. Chem. Phys. 1981, 74: 5838