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Synlett 2005(9): 1447-1449
DOI: 10.1055/s-2005-868488
DOI: 10.1055/s-2005-868488
LETTER
© Georg Thieme Verlag Stuttgart · New York
Deoxygenation of Sulfoxides and Reductive Coupling of Sulfonyl Chlorides, Sulfinates and Thiosulfonates Using Silphos [PCl3-n(SiO2)n] as a Heterogeneous Phosphine Reagent
Further Information
Received
3 January 2005
Publication Date:
25 April 2005 (online)
Publication History
Publication Date:
25 April 2005 (online)
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Abstract
Deoxygenation of sulfoxides to thioethers and reductive coupling of sulfonyl chlorides, sodium sulfinates and thiosulfonates to their corresponding disulfides were carried out by a heterogeneous phosphine reagent, Silphos [PCl3-n(SiO2)n] and molecular I2 in dry refluxing MeCN in high yields.
Key words
deoxygenation - thioethers - reductive coupling - sulfonyl chlorides - disulfides - Silphos - heterogeneous phosphine
-
1a
Madesclaire M. Tetrahedron 1988, 21: 6537 -
1b
Drabowicz J.Togo H.Mikolajczyk M.Oae S. Org. Prep. Proced. Int. 1984, 16: 171 -
1c
Schmizu M.Shibuya K.Hayakawa R. Synlett 2000, 1437 -
1d
Khurana JM. Tetrahedron Lett. 1998, 39: 3829 -
1e
Yadav JS.Reddy BVS.Srinivas C.Srihari P. Synlett 2001, 854 -
1f
Balicki R. Synthesis 1991, 155 -
1g
Miller SJ.Collier TR.Wu W. Tetrahedron Lett. 2000, 41: 3781 -
1h
Firouzabadi H.Karimi B. Synthesis 1999, 500 -
1i
Firouzabadi H.Jamalian A. Phosphorus, Sulfur Silicon Relat. Elem. 2001, 170: 211 -
1j
Yoo BW.Choi KH.Kim DY.Choi KI.Kim JH. Synth. Commun. 2003, 33: 53 -
1k
Iranpoor N.Firouzabadi H.Shaterian HR. J. Org. Chem. 2002, 67: 2826 -
1l
Karimi B.Zareyee D. Synthesis 2003, 335 -
1m
Guedes da Silva MFC.Pombeiro AJL.Geremia S.Zangrando E.Calligaris M.Zinchenko AV.Kukushkin VY. J. Chem. Soc., Dalton Trans. 2000, 1363 -
1n
Shimizu M.Shibuya K.Hayakawa R. Synlett 2000, 1437 -
1o
Miller SJ.Collier TR.Wu W. Tetrahedron Lett. 2000, 41: 3781 -
1p
Nicolaou KC.Koumbis AE.Snyder SA.Simonsen KB. Angew. Chem. Int. Ed. 2000, 39: 2529 -
1q
Mohanazadeh F.Momeni AR.Ranjbar Y. Tetrahedron Lett. 1994, 35: 6127 - 2
Sanz R.Escribano J.Aguado R.Pedrosa MR.Arnáiz FJ. Synthesis 2004, 1629 - 3
Amonoo-Neizer EH.Ray SK.Shaw RA.Smith BC. J. Chem. Soc. 1965, 4296 - 4
Oae S.Nakanishi A.Kozuka S. Tetrahedron 1972, 28: 549 - 5
Castrillón JPA.Szmant HH. J. Org. Chem. 1965, 30: 1338 -
6a
Dreux M.Leroux Y.Savignac P. Synthesis 1974, 506 -
6b
Chaser DW.Pratt TM. Synthesis 1976, 262 - 7
Singh SP.Saxena RK. Synth. Commun. 1987, 17: 575 - 8
Olah GA.Gupta BGB.Narang SC. J. Org. Chem. 1978, 43: 4503 - 9
Sekine M.Yamagata H.Hata T. Tetrahedron Lett. 1979, 375 - 10
Granoth I.Kalir A.Pelah Z. J. Chem. Soc. C 1969, 2424 - 11
Denis JN.Krief A. J. Chem. Soc., Chem. Commun. 1980, 544 - 12
Denis JN.Krief A. Tetrahedron Lett. 1979, 3995 - 13
Jie Z.Rammoorty V.Fischer B. J. Org. Chem. 2002, 67: 711 - 14
Iranpoor N.Firouzabadi H.Jamalian A.Kazemi F. Tetrahedron 2005, in press - 16
Mayer A.Montanaria F.Tramontini M. Gazz. Chim. Ital. 1960, 90: 739 - 17
Tsujiara K.Furukawa N.Oac S. Bull. Chem. Soc. Jpn. 1969, 42: 2631 - 19 Beilstein’s Handbuch der Organischen Chemie Springer Verlag; Berlin: 1923.
- 20
Fujiki K.Kurita S.Yoshida E. Synth. Commun. 1996, 26: 3619
References
Fluka Chemie, Chemica-Biochemica 1993-94.
18Handbook of Chemistry and Physics, 54th ed., 1973-74.