Chemoselective (Trans)thioacetalization of Carbonyl Compounds with a Reusable Lewis Acid-Surfactant-Combined Copper Bis(dodecyl sulfate) Catalyst in Water

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS)₂] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields.

References

• 1 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley & Sons; New York: 1999.  p.329 
  Google Scholar
• 2a Corey EJ. Seebach D. Angew. Chem., Int. Ed. Engl.  1965,  4:  1075 
  Google Scholar
• 2b Seebach D. Corey EJ. J. Org. Chem.  1975,  40:  231 
  Google Scholar
• 2c Grobel BT. Seebach D. Synthesis  1977,  357 
  Google Scholar
• 2d Seebach D. Angew. Chem., Int. Ed. Engl.  1979,  18:  239 
  Google Scholar
• 2e Smith AB. Christopher MA. Acc. Chem. Res.  2004,  37:  365 
  Google Scholar
• 3a Yus M. Nájera C. Foubelo F. Tetrahedron  2003,  59:  6147 
  Google Scholar
• 3b Smith AB. Pitram SM. Gaunt MJ. Kozmin SA. J. Am. Chem. Soc.  2002,  124:  14516 
  Google Scholar
• 3c Takeda T. Kuroi S. Yanai K. Tsubouchi A. Tetrahedron Lett.  2002,  43:  5641 
  Google Scholar
• 3d Smith AB. Lin Q. Doughty VA. Zhuang L. McBriar MD. Kerns JK. Brook CS. Murase N. Nakayama K. Angew. Chem. Int. Ed.  2001,  40:  196 
  Google Scholar
• 3e Breit B. Angew. Chem. Int. Ed.  1998,  37:  453 
  Google Scholar
• 3f Horikawa Y. Watanabe M. Fujiwara T. Takeda T. J. Am. Chem. Soc.  1997,  119:  1127 
  Google Scholar
• 4 Truce WE. Roberts FE. J. Org. Chem.  1963,  28:  961 
  CrossrefGoogle Scholar
• 5 Garlaschelli L. Vidari G. Tetrahedron Lett.  1990,  31:  5815 
  CrossrefGoogle Scholar
• 6 Patney HK. Tetrahedron Lett.  1991,  32:  2259 
  CrossrefGoogle Scholar
• 7a Khan AT. Parvin T. Choudhury LH. Synthesis  2006,  2497 
  Google Scholar
• 7b Kamitori T. Hojo K. Masuda R. Kimura T. Yoshida T. J. Org. Chem.  1986,  51:  1427 
  Google Scholar
• 8a Patney HK. Margan S. Tetrahedron Lett.  1996,  37:  4621 
  Google Scholar
• 8b Firouzabadi H. Iranpoor N. Karimi B. Synlett  1999,  319 
  Google Scholar
• 9 Anand R. Saravanan VP. Singh VK. Synlett  1999,  415 
  Article in Thieme ConnectGoogle Scholar
• 10 Ong BS. Tetrahedron Lett.  1980,  21:  4225 
  CrossrefGoogle Scholar
• 11 Tani H. Masumoto K. Inamasu T. Tetrahedron Lett.  1991,  32:  2039 
  CrossrefGoogle Scholar
• 12 Das NB. Nayak A. Sharma RP. J. Chem. Res., Synop.  1993,  242 
  Google Scholar
• 13 Ku B. Oh DY. Synth. Commun.  1989,  19:  433 
  CrossrefGoogle Scholar
• 14 Kumar V. Dev S. Tetrahedron Lett.  1983,  24:  1289 
  CrossrefGoogle Scholar
• 15a Muthusamy S. Babu SA. Gunanathan C. Tetrahedron Lett.  2001,  42:  359 
  Google Scholar
• 15b Muthusamy S. Babu SA. Gunanathan C. Synth. Commun.  2001,  31:  1205 
  Google Scholar
• 16 Fieser LF. J. Am. Chem. Soc.  1954,  76:  1945 
  CrossrefGoogle Scholar
• 17 Corey EJ. Shimoji K. Tetrahedron Lett.  1983,  24:  169 
  CrossrefGoogle Scholar
• 18a Firouzabadi H. Iranpoor N. Hazarkhani H. J. Org. Chem.  2001,  66:  7527 
  Google Scholar
• 18b Deka N. Sarma JC. Chem. Lett.  2001,  749 ; and references cited therein
  Google Scholar
• 19 Perni RB. Synth. Commun.  1989,  19:  2383 
  CrossrefGoogle Scholar
• 20 Saraswathy VG. Sankararaman S. J. Org. Chem.  1994,  59:  4665 
  CrossrefGoogle Scholar
• 21 De S K. Synthesis  2004,  2837 
  Article in Thieme ConnectGoogle Scholar
• 22 De S K. Tetrahedron Lett.  2004,  45:  1035 
  CrossrefGoogle Scholar
• 23 Firouzabadi H. Iranpoor N. Karimi B. Synlett  1998,  739 
  Article in Thieme ConnectGoogle Scholar
• 24 Kazahaya K. Tsuneo S. Sato T. Synlett  2004,  1640 
  Article in Thieme ConnectGoogle Scholar
• 25 Kamal A. Chouhan G. Synlett  2002,  474 
  Article in Thieme ConnectGoogle Scholar
• 26a Kamal A. Chouhan G. Tetrahedron Lett.  2002,  43:  1347 
  Google Scholar
• 26b Kamal A. Chouhan G. Tetrahedron Lett.  2003,  44:  3337 
  Google Scholar
• 26c De S K. Synthesis  2004,  828 
  Google Scholar
• 27 De S K. J. Mol. Catal. A: Chem.  2005,  232:  77 
  CrossrefGoogle Scholar
• 28a Organic Synthesis in Water   Grieco PA. Blackie Academic & Professional; London: 1998. 
  Google Scholar
• 28b Li C.-J. Chan T.-H. Organic Reactions in Aqueous Media   Wiley & Sons; New York: 1997. 
  Google Scholar
• 28c Breslow R. Acc. Chem. Res.  1991,  24:  159 
  Google Scholar
• 29a Manabe K. Sun X.-M. Kobayashi S. J. Am. Chem. Soc.  2001,  123:  10101 
  Google Scholar
• 29b Manabe K. Iimura S. Sun X.-M. Kobayashi S. J. Am. Chem. Soc.  2002,  124:  11971 
  Google Scholar
• 29c Mori Y. Manabe K. Kobayashi S. Angew. Chem. Int. Ed.  2001,  40:  2815 
  Google Scholar
• 29d Kobayashi S. Manabe K. Acc. Chem. Res.  2002,  35:  209 ; and references cited therein
  Google Scholar
• 30a Otto S. Engberts JBFN. Kwak JCT. J. Am. Chem. Soc.  1998,  120:  9517 
  Google Scholar
• 30b Otto S. Engberts JBFN. Kwak JCT. J. Am. Chem. Soc.  1999,  121:  6798 
  Google Scholar
• 31a Kobayashi S. Mori Y. Nagayama S. Manabe K. Green Chem.  1999,  1:  175 
  Google Scholar
• 31b Manabe K. Mori Y. Kobayashi S. Synlett  1999,  1401 
  Google Scholar
• 31c Manabe K. Kobayashi S. Org. Lett.  1999,  1:  1965 
  Google Scholar
• 31d Manabe K. Mori Y. Kobayashi S. Tetrahedron  2001,  57:  2537 
  Google Scholar
• 31e Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1426 
  Google Scholar
• 32 Ceschi M. Felix ALDA. Peppe C. Tetrahedron Lett.  2000,  41:  9695 
  CrossrefGoogle Scholar
• 33a Moroi Y. Motomura K. Matuura R. J. Colloid Interface Sci.  1974,  46:  111 
  Google Scholar
• 33b Kamenka N. Burgaud I. Treiner C. Zana R. Langmuir  1994,  10:  3455 
  Google Scholar
• 34a Satake I. Iwamatsu I. Hosokawa S. Matuura R. Bull. Chem. Soc. Jpn.  1963,  36:  204 
  Google Scholar
• 34b Satake I. Matuura R. Bull. Chem. Soc. Jpn.  1963,  36:  813 
  Google Scholar
• Several catalytic transthioacetalization systems are faster and more efficient than direct thioacetalization; see:
• 35a Muthusamy A. Babu SA. Gunanathan C. Tetrahedron  2002,  58:  7897 
  Google Scholar
• 35b Ranu BC. Das A. Samanta S. Synlett  2002,  727 
  Google Scholar
• 36 Sato T. Otera J. Nozaki H. J. Org. Chem.  1993,  58:  4971 
  CrossrefGoogle Scholar