Deoxygenation of Sulfoxides and Reductive Coupling of Sulfonyl Chlorides, Sulfinates and Thiosulfonates Using Silphos [PCl3-n(SiO2)n] as a Heterogeneous Phosphine Reagent

Nasser Iranpoor; Habib Firouzabadi; Arezu Jamalian

doi:10.1055/s-2005-868488

LETTER

Deoxygenation of Sulfoxides and Reductive Coupling of Sulfonyl Chlorides, Sulfinates and Thiosulfonates Using Silphos [PCl_3-n(SiO₂)_n] as a Heterogeneous Phosphine Reagent

Nasser Iranpoor*, Habib Firouzabadi*, Arezu Jamalian
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2280926; e-Mail: iranpoor@chem.susc.ac.ir; e-Mail: firouzabadi@chem.susc.ac.ir;

Abstract

All articles of this category

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 [PCl_3-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

Full Text

References

<A NAME="RD00205ST-1A">1a</A> Madesclaire M. Tetrahedron 1988, 21: 6537

<A NAME="RD00205ST-1B">1b</A> Drabowicz J. Togo H. Mikolajczyk M. Oae S. Org. Prep. Proced. Int. 1984, 16: 171

<A NAME="RD00205ST-1C">1c</A> Schmizu M. Shibuya K. Hayakawa R. Synlett 2000, 1437

<A NAME="RD00205ST-1D">1d</A> Khurana JM. Tetrahedron Lett. 1998, 39: 3829

<A NAME="RD00205ST-1E">1e</A> Yadav JS. Reddy BVS. Srinivas C. Srihari P. Synlett 2001, 854

<A NAME="RD00205ST-1F">1f</A> Balicki R. Synthesis 1991, 155

<A NAME="RD00205ST-1G">1g</A> Miller SJ. Collier TR. Wu W. Tetrahedron Lett. 2000, 41: 3781

<A NAME="RD00205ST-1H">1h</A> Firouzabadi H. Karimi B. Synthesis 1999, 500

<A NAME="RD00205ST-1I">1i</A> Firouzabadi H. Jamalian A. Phosphorus, Sulfur Silicon Relat. Elem. 2001, 170: 211

<A NAME="RD00205ST-1J">1j</A> Yoo BW. Choi KH. Kim DY. Choi KI. Kim JH. Synth. Commun. 2003, 33: 53

<A NAME="RD00205ST-1K">1k</A> Iranpoor N. Firouzabadi H. Shaterian HR. J. Org. Chem. 2002, 67: 2826

<A NAME="RD00205ST-1L">1l</A> Karimi B. Zareyee D. Synthesis 2003, 335

<A NAME="RD00205ST-1M">1m</A> Guedes da Silva MFC. Pombeiro AJL. Geremia S. Zangrando E. Calligaris M. Zinchenko AV. Kukushkin VY. J. Chem. Soc., Dalton Trans. 2000, 1363

<A NAME="RD00205ST-1N">1n</A> Shimizu M. Shibuya K. Hayakawa R. Synlett 2000, 1437

<A NAME="RD00205ST-1O">1o</A> Miller SJ. Collier TR. Wu W. Tetrahedron Lett. 2000, 41: 3781

<A NAME="RD00205ST-1P">1p</A> Nicolaou KC. Koumbis AE. Snyder SA. Simonsen KB. Angew. Chem. Int. Ed. 2000, 39: 2529

<A NAME="RD00205ST-1Q">1q</A> Mohanazadeh F. Momeni AR. Ranjbar Y. Tetrahedron Lett. 1994, 35: 6127

<A NAME="RD00205ST-2">2</A> Sanz R. Escribano J. Aguado R. Pedrosa MR. Arnáiz FJ. Synthesis 2004, 1629

<A NAME="RD00205ST-3">3</A> Amonoo-Neizer EH. Ray SK. Shaw RA. Smith BC. J. Chem. Soc. 1965, 4296

<A NAME="RD00205ST-4">4</A> Oae S. Nakanishi A. Kozuka S. Tetrahedron 1972, 28: 549

<A NAME="RD00205ST-5">5</A> Castrillón JPA. Szmant HH. J. Org. Chem. 1965, 30: 1338

<A NAME="RD00205ST-6A">6a</A> Dreux M. Leroux Y. Savignac P. Synthesis 1974, 506

<A NAME="RD00205ST-6B">6b</A> Chaser DW. Pratt TM. Synthesis 1976, 262

<A NAME="RD00205ST-7">7</A> Singh SP. Saxena RK. Synth. Commun. 1987, 17: 575

<A NAME="RD00205ST-8">8</A> Olah GA. Gupta BGB. Narang SC. J. Org. Chem. 1978, 43: 4503

<A NAME="RD00205ST-9">9</A> Sekine M. Yamagata H. Hata T. Tetrahedron Lett. 1979, 375

<A NAME="RD00205ST-10">10</A> Granoth I. Kalir A. Pelah Z. J. Chem. Soc. C 1969, 2424

<A NAME="RD00205ST-11">11</A> Denis JN. Krief A. J. Chem. Soc., Chem. Commun. 1980, 544

<A NAME="RD00205ST-12">12</A> Denis JN. Krief A. Tetrahedron Lett. 1979, 3995

<A NAME="RD00205ST-13">13</A> Jie Z. Rammoorty V. Fischer B. J. Org. Chem. 2002, 67: 711

<A NAME="RD00205ST-14">14</A> Iranpoor N. Firouzabadi H. Jamalian A. Kazemi F. Tetrahedron 2005, in press

Fluka Chemie, Chemica-Biochemica 1993-94.

<A NAME="RD00205ST-16">16</A> Mayer A. Montanaria F. Tramontini M. Gazz. Chim. Ital. 1960, 90: 739

<A NAME="RD00205ST-17">17</A> Tsujiara K. Furukawa N. Oac S. Bull. Chem. Soc. Jpn. 1969, 42: 2631

Handbook of Chemistry and Physics, 54^th ed., 1973-74.

<A NAME="RD00205ST-19">19</A> Beilstein’s Handbuch der Organischen Chemie Springer Verlag; Berlin: 1923.

<A NAME="RD00205ST-20">20</A> Fujiki K. Kurita S. Yoshida E. Synth. Commun. 1996, 26: 3619