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 2002(15): 2259-2265
DOI: 10.1055/s-2002-34838
DOI: 10.1055/s-2002-34838
PAPER
© Georg Thieme Verlag Stuttgart · New York
CAN Mediated Reaction of Aryl
Sulfinates with Alkenes and Alkynes:
Synthesis of Vinyl
Sulfones, β-Iodovinyl Sulfones and Acetylenic Sulfones
Further Information
Received
30 April 2002
Publication Date:
21 October 2002 (online)
Publication History
Publication Date:
21 October 2002 (online)
Abstract
Cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate afforded the corresponding acetylenic sulfones in high yields.
Key words
cerium(IV) ammonium nitrate - sulfonylation - aryl alkenes - alkenes - acetylenes - vinyl sulfones - β-iodovinyl sulfones - acetylenic sulfones
-
1a
Heiba EI.Dessau RM. J. Am. Chem. Soc. 1971, 93: 524 -
1b
Baciocchi E.Ruzziconi R. Synth. Commun. 1988, 18: 1841 -
1c
Baciocchi E.Ruzziconi R. J. Org. Chem. 1986, 51: 1645 - 2
Nair V.Mathew J.Prabhakaran J. Chem. Soc. Rev. 1997, 127 ; and references cited therein - 3
Trahanovsky WS.Robbins MD. J. Am. Chem. Soc. 1971, 93: 5256 - 4
Lemieux RU.Ratcliffe RM. Can. J. Chem. 1979, 93: 5256 - 5
Nair V.Nair LG. Tetrahedron Lett. 1998, 39: 4585 - 6
Nair V.George TG.Nair LG.Panicker SB. Tetrahedron Lett. 1999, 40: 1105 - 7
Nair V.George TG. Tetrahedron Lett. 2000, 41: 3199 - 8
Nair V.Nair LG.George TG.Augustine A. Tetrahedron 2000, 56: 7607 - 9
Nair V.Augustine A.George TG. Eur. J. Org. Chem. 2002, 2363 - 10
Nair V.George TG.Sheeba V.Augustine A.Balagopal L.Nair LG. Synlett 2000, 1597 - 11
Nair V.Augustine A.George TG.Nair LG. Tetrahedron Lett. 2001, 42: 6763 - 12
Popoff IC.Denver JL. J. Org. Chem. 1969, 34: 1128 - 13
Ley SV.Simpkins NS. J. Chem. Soc., Chem Commun. 1983, 1281 - 14
Gancarz RA.Kice JL. Tetrahedron Lett. 1980, 4155 -
15a
Asscher M.Vofsi D. J. Chem. Soc. 1964, 4962 -
15b
Asscher M.Vofsi D. J. Chem. Soc., Perkin Trans. 1 1972, 1543 -
15c
Hopkins PB.Fuchs PL. J. Org. Chem. 1978, 43: 1208 -
16a
Fuchs PL.Braish TF. Chem. Rev. 1986, 86: 903 -
16b
De Lucci O.Pasquato L. Tetrahedron 1988, 44: 6755 -
17a
Truce WE.Heuring DL.Wolf GC. J. Org. Chem. 1974, 39: 238 -
17b
Iwata N.Morioka T.Kobayashi T.Asada T.Kinoshita H.Inomata K. Bull. Chem. Soc. Jpn. 1992, 65: 1379 -
17c
Harwood LM.Julia M.Thuillier GLe. Tetrahedron 1980, 36: 2483 -
17d
Short KM.Ziegler CB. Tetrahedron Lett. 1993, 34: 71 -
17e
Zoller T.Uguen D.Cian AD.Fischer J. Tetrahedron Lett. 1998, 39: 8089 -
18a
Truce WE.Goralski CT.Christensen LW.Bavry RH. J. Org. Chem. 1970, 35: 4217 -
18b
Amiel Y. Tetrahedron Lett. 1971, 661 -
18c
Amiel Y. J. Org. Chem. 1971, 36: 3691 -
18d
Amiel Y. J. Org. Chem. 1974, 39: 3867 -
18e
Truce WE.Wolf GC. J. Chem. Soc., Chem. Commun. 1969, 150 -
19a
Gancarz RA.Kice JL. J. Org. Chem. 1981, 46: 4899 -
19b
Inomata K.Sasaoka S.Morioka T.Kobayashi T.Tanaka Y.Igarashi S.Ohtani T.Kinoshita S.Kotake H. Bull. Chem. Soc. Jpn. 1987, 60: 1767 -
19c
Duan DH.Huang X. Synlett 1999, 317 - 20
Kamigata N.Sawada H.Kobayashi M. J. Org. Chem. 1983, 48: 3793 -
21a
Jang WB.Jeon HJ.Oh DY. Synth. Commun. 1998, 28: 1253 -
21b
Lee WJ.Lee C.-W.Jung JH.Oh DY. Synth. Commun. 2000, 30: 279 -
22a
Narasaka K.Mochizuki T.Hayakawa S. Chem. Lett. 1994, 1705 -
22b
Mochizuki T.Hayakawa S.Narasaka K. Bull. Chem. Soc. Jpn. 1996, 69: 2517 -
22c
Bordwell FG.Kern RJ. J. Am. Chem. Soc. 1955, 77: 1141 - 23
Truce WE.Wolf GC. J. Org. Chem. 1971, 36: 1727 - 24
Harwood LM.Julia M.Le Thuillier G. Tetrahedron 1980, 36: 2483 -
25a
Suzuki H.Abe H. Tetrahedron Lett. 1996, 37: 3717 -
25b
Lee JW.Oh DY. Synlett 1990, 290