TAPC-Promoted Synthesis of
Sulfonyl Chlorides from Sulfonic Acids

Kiumars Bahrami

doi:10.1055/s-0031-1289547

LETTER

TAPC-Promoted Synthesis of Sulfonyl Chlorides from Sulfonic Acids

Kiumars Bahrami*^a,b
^a Department of Organic Chemistry, Faculty of Chemistry, Razi University, Kermanshah 67149-67346, Iran
Fax: +98(831)4274559; e-Mail: kbahrami2@hotmail.com;
^b Nanoscience and Nanotechnology Research Center (NNRC), Razi University, Kermanshah 67149-67346, Iran

Abstract

Alle Artikel dieser Rubrik

Abstract

A novel and efficient method is described for the preparation of sulfonyl chlorides from sulfonic acids using TAPC as chlorinating agent. Mild reaction conditions, shorter reaction times, high efficiencies, cost-effectiveness, and facile isolation of the desired products make the present methodology a practical alternative and will provide a valuable synthetic tool for various pharmaceutical applications.

Key words

sulfonyl chlorides - sulfonic acids - chlorinating agent - solvent-free conditions - 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)

Volltext

Referenzen

References

<A NAME="RB15211ST-1A">1a</A> Langler RF. Marini ZA. Spalding ES. Can. J. Chem. 1979, 57: 3193

<A NAME="RB15211ST-1B">1b</A> March J. Advanced Organic Chemistry John Wiley and Sons; New York: 1985. p.1348

<A NAME="RB15211ST-2">2</A> Barbero M. Cadamuro S. Degani I. Fochi R. Regondi V. Synthesis 1989, 957

<A NAME="RB15211ST-3A">3a</A> Watson RJ. Batty D. Baxter AD. Hannah DR. Owen DA. Montana JG. Tetrahedron Lett. 2002, 43: 683

<A NAME="RB15211ST-3B">3b</A> Percec V. Bera TK. De B B. Sanai Y. Smith J. Holerca MN. Barboiu B. Grubbs RB. Fréchet JMJ. J. Org. Chem. 2001, 66: 2104

<A NAME="RB15211ST-3C">3c</A> Chen Z. Demuth TP. Wireko FC. Bioorg. Med. Chem. Lett. 2002, 11: 2111

<A NAME="RB15211ST-4A">4a</A> Monnee MCF. Marijne MF. Brouwer AJ. Liskamp RMJ. Tetrahedron Lett. 2000, 41: 7991

<A NAME="RB15211ST-4B">4b</A> Piatek A. Chapuis C. Jurczak J. Helv. Chim. Acta 2002, 85: 1973

<A NAME="RB15211ST-4C">4c</A> Humljan J. Gobec S. Tetrahedron Lett. 2005, 46: 4069

<A NAME="RB15211ST-5">5</A> Kværnø L. Werder M. Hauser H. Carreira EM. Org. Lett. 2005, 7: 1145

<A NAME="RB15211ST-6">6</A> Meinzer A. Breckel A. Thaher BA. Manicone N. Otto H.-H. Helv. Chim. Acta 2004, 87: 90

<A NAME="RB15211ST-7">7</A> Park YJ. Shin HH. Kim YH. Chem. Lett. 1992, 1483

<A NAME="RB15211ST-8">8</A> Schindler W. Helv. Chim. Acta 1957, 40: 2148

<A NAME="RB15211ST-9">9</A> Bossard HH. Mory R. Schmid M. Zollinger H. Helv. Chim. Acta 1959, 42: 1653

<A NAME="RB15211ST-10">10</A> Fujita S. Synthesis 1982, 423

<A NAME="RB15211ST-11">11</A> Barco A. Benetti S. Pollini P. Tadia R. Synthesis 1974, 877

<A NAME="RB15211ST-12">12</A> Blotny G. Tetrahedron Lett. 2003, 44: 1499

<A NAME="RB15211ST-13A">13a</A> Schenk R. Römer G. Ber. Dtsch. Chem. Ges. 1924, 57: 1343

<A NAME="RB15211ST-13B">13b</A> Allcock HR. J. Am. Chem. Soc. 1964, 86: 2591

<A NAME="RB15211ST-13C">13c</A> Graham JC. Marr DH. Can. J. Chem. 1972, 50: 3857

<A NAME="RB15211ST-13D">13d</A> Hashimoto M. Obora Y. Sakaguchi S. Ishii Y. J. Org. Chem. 2008, 73: 2894

<A NAME="RB15211ST-13E">13e</A> Voznicova RK. Taraba J. Prihoda J. Alberti M. Polyhedron 2008, 27: 2077

<A NAME="RB15211ST-13F">13f</A> Allcock HR. Desorcie JL. Harris PJ. J. Am. Chem. Soc. 1983, 105: 2814

<A NAME="RB15211ST-13G">13g</A> Rolland O. Griffe L. Poupot M. Maraval A. Ouali A. Coppel Y. Fournie JJ. Bacquet G. Turrin CO. Caminade AM. Majoral JP. Poupot R. Chem. Eur. J. 2008, 14: 4836

<A NAME="RB15211ST-14A">14a</A> Bahrami K. Khodaei MM. Kavianinia I. Synthesis 2007, 547

<A NAME="RB15211ST-14B">14b</A> Bahrami K. Khodaei MM. Naali F. J. Org. Chem. 2008, 73: 6835

<A NAME="RB15211ST-14C">14c</A> Bahrami K. Khodaei MM. Tirandaz Y. Synthesis 2009, 369

<A NAME="RB15211ST-14D">14d</A> Khodaei MM. Bahrami K. Tirandaz Y. J. Sulfur Chem. 2009, 30: 581

<A NAME="RB15211ST-14E">14e</A> Bahrami K. Khodaei MM. Farrokhi A. Tetrahedron 2009, 65: 7658

<A NAME="RB15211ST-14F">14f</A> Bahrami K. Khodaei MM. Soheilizad M. Synlett 2009, 2773

<A NAME="RB15211ST-14G">14g</A> Bahrami K. Khodaei MM. Soheilizad M. J. Org. Chem. 2009, 74: 9287

<A NAME="RB15211ST-14H">14h</A> Bahrami K. Tetrahedron Lett. 2006, 47: 2009

<A NAME="RB15211ST-14I">14i</A> Khodaei MM. Bahrami K. Khedri M. Can. J. Chem. 2007, 85: 7

<A NAME="RB15211ST-14J">14j</A> Khodaei MM. Bahrami K. Karimi A. Synthesis 2008, 1682

<A NAME="RB15211ST-14K">14k</A> Bahrami K. Khodaei MM. Karimi A. Synthesis 2008, 2543

<A NAME="RB15211ST-14L">14l</A> Bahrami K. Khodaei MM. Naali F. Synlett 2009, 569

<A NAME="RB15211ST-14M">14m</A> Khodaei MM. Bahrami K. Sheikh Arabi M. J. Sulfur Chem. 2010, 31: 83

<A NAME="RB15211ST-14N">14n</A> Bahrami K. Khodaei MM. Sheikh Arabi M. Tetrahedron Lett. 2010, 51: 6939

<A NAME="RB15211ST-14O">14o</A> Bahrami K. Khodaei MM. Soheilizad M. Tetrahedron Lett. 2010, 51: 4843

<A NAME="RB15211ST-14P">14p</A> Bahrami K. Khodaei MM. Tajik M. Synthesis 2010, 4282

<A NAME="RB15211ST-14Q">14q</A> Bahrami K. Khodaei MM. Sheikh Arabi M. J. Org. Chem. 2010, 75: 6208

<A NAME="RB15211ST-14R">14r</A> Bahrami K. Khodaei MM. Nejati A. Green Chem. 2010, 12: 1237

<A NAME="RB15211ST-14S">14s</A> Bahrami K. Khodaei MM. Fattahpour P. Catal. Sci. Technol. 2011, 1: 389

<A NAME="RB15211ST-15">15</A> Nishiguchi A. Maeda K. Miki S. Synthesis 2006, 4131

<A NAME="RB15211ST-16">16</A> Pu Y.-M. Christesen A. Ku Y.-Y. Tetrahedron Lett. 2010, 51: 418

<A NAME="RB15211ST-17">17</A> Ballistreri FP. Tomaselli GA. Toscano RM. Tetrahedron Lett. 2008, 49: 3291

<A NAME="RB15211ST-18">18</A> Steinman R. Schirmer FB. Audrieth LF. J. Am. Chem. Soc. 1942, 64: 2377