Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 8
414
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Prins Cyclization of Styrenes or Acetophenone Catalyzed by DBSA in Water

, , , , &
Pages 1234-1242 | Received 27 Sep 2010, Published online: 22 Dec 2011

REFERENCES

  • For recent reviews on organic reactions in water, see (a) Butler , R. N. ; Coyne , A. G. Water: Nature's reaction enforcers comparative effects for organic synthesis “in-water” and “on-water.” Chem. Rev. 2010 , 110 , 6302 – 6337 ; (b) Li , C.-J. Organic reactions in aqueous media with a focus on carbon–carbon bond formations: A decade update . Chem. Rev. 2005 , 105 , 3095 – 3166 ; (c) Li , C.-J. ; Chen , L. Organic chemistry in water . Chem. Soc. Rev. 2006 , 35 , 68 – 82 ; (d) Lindström , U. M. Stereoselective organic reactions in water . Chem. Rev. 2002 , 102 , 2751 – 2772 ; (e) Kobayashi , S. Asymmetric catalysis in aqueous media . Pure Appl. Chem. 2007 , 79 , 235 – 245 .
  • For recent reported strategies for organic reactions in water, see (a) Gu , Y. ; Ogawa , C. ; Kobayashi , J. ; Mori , Y. ; Kobayashi , S. A heterogeneous silica-supported scandium/ionic liquid catalyst system for organic reactions in water . Angew. Chem. Int. Ed. 2006 , 45 , 7217 – 7220 ; (b) Murthy , S. N. ; Madhav , B. ; Reddy , V. P. ; Nageswar , Y. V. D. One-pot synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives using β-cyclodextrin as reusable catalyst in water . Tetrahedron Lett. 2010 , 51 , 3649 – 3653 ; (c) Senra , J. D. ; Malta , L. F. B. ; da Costa , M. E. H. M. ; Michel , R. C. ; Aguiar , L. C. S. ; Simas , A. B. C. ; Antunes , O. A. C. Hydroxypropyl-α-cyclodextrin-capped palladium nanoparticles: Active scaffolds for efficient carbon-carbon bond-forming cross-couplings in water . Adv. Synth. Catal. 2009 , 351 , 2411 – 2422 ; (d) Gu , Y. ; Ogawa , C. ; Kobayashi , S. Silica-supported sodium sulfonate with ionic liquid: A neutral catalyst system for Michael reactions of indoles in water . Org. Lett. 2007 , 9 , 175 – 178 .
  • Selected examples: (a) Manabe , K. ; Sun , X.-M. ; Kobayashi , S. Dehydration reactions in water: Surfactant-type Brønsted acid-catalyzed direct esterification of carboxylic acids with alcohols in an emulsion system . J. Am. Chem. Soc. 2001 , 123 , 10101 – 10102 ; (b) Manabe , K. ; Iimura , S. ; Sun , X.-M. ; Kobayashi , S. Dehydration reactions in water: Brønsted acid-surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water . J. Am. Chem. Soc. 2002 , 124 , 11971 – 11978 .
  • See reviews: (a) Shiri , M. ; Zolfigol , M. A. Surfactant-type catalysts in organic reactions . Tetrahedron 2009 , 65 , 587 – 598 ; (b) Ogawa , C. ; Kobayashi , S. Acid catalysis in water. In Organic Reactions in Water; U. M. Lindstroem (Ed.); Blackwell: Oxford, UK, 2007; pp. 60–91.
  • Selected examples: (a) Karam , A. ; Villandier , N. ; Delample , M. ; Koerkamp , C. K. ; Douliez , J.-P. ; Granet , R. ; Krausz , P. ; Barrault , J. ; Jerome , F. Rational design of sugar-based-surfactant combined catalysts for promoting glycerol as a solvent . Chem. Eur. J. 2008 , 14 , 10196 – 10200 ; (b) Firouzabadi , H. ; Iranpoor , N. ; Jafari , A. A. Micellar solution of sodium dodecyl sulfate (SDS) catalyzes facile Michael addition of amines and thiols to α,β-unsaturated ketones in water under neutral conditions . Adv. Synth. Catal. 2005 , 347 , 655 – 661 ; (c) Watanabe , Y. ; Sawada , K. ; Hayashi , M. A green method for the self-aldol condensation of aldehydes using lysine . Green Chem. 2010 , 12 , 384 – 386 .
  • Pastor , I. M. ; Yus , M. The Prins reaction: Advances and applications . Curr. Org. Chem. 2007 , 11 , 925 – 957 .
  • Arundale , E. ; Mikeska , L. A. The olefin-aldehyde condensation: The Prins reaction , Chem. Rev. 1952 , 51 , 505 – 555 .
  • Some recent examples: (a) Yadav , J. S. ; Reddy , B. V. S. ; Bhaishya , G. InBr3-[bmim]PF6: A novel and recyclable catalytic system for the synthesis of 1,3-dioxane derivatives. Green Chem. 2003, 5, 264–266; (b) Li , G. ; Gu , Y. ; Ding , Y. ; Zhang , H. ; Wang , J. ; Gao , Q. ; Yan , L. ; Suo , J. Wells–Dawson-type molybdovanadophosphoric heteropoly acids–catalyzed Prins cyclization of alkenes with paraformaldehyde under mild conditions—a facile and efficient method to 1,3-dioxane derivatives. J. Mol. Catal. A: Chem. 2004, 218, 147–152; (c) Bach , T. ; Löbel , J. Selective Prins reaction of styrenes and formaldehyde catalyzed by 2,6-di-tert-butylphenoxy(difluoro)borane. Synthesis 2002, 2521–2526; (d) Yadav , J. S. ; Reddy , B. V. S. ; Gopal , A. V. H. ; Kumar , G. G. K. S. N. ; Madavi , C. ; Kunwar , A. C. Iodine as a mild and versatile reagent for the synthesis of 1,3-dioxane derivatives via the Prins reaction. Tetrahedron Lett. 2008, 49, 4420–4423; (e) Reddy , S. S. ; Raju , B. D. ; Kumar , V. S. ; Padmasri , A. H. ; Narayanan , S. ; Rao , K. S. R. Sulfonic acid functionalized mesoporous SBA-15 for selective synthesis of 4-phenyl-1,3-dioxane. Catal. Commun. 2007, 8, 261–266.
  • (a) Gu , Y. ; Ogawa , C. ; Kobayashi , S. Novel hydrophobic Brønsted acidic ionic liquids as efficient and reusable catalysts for organic reactions in water . Chem. Lett. 2006 , 35 , 1176 – 1177 ; (b) Du , Y. ; Tian , F. Efficient synthesis of 1,3-dioxanes catalyzed by trifluoromethanesulfonic acid using formalin as formaldehyde source . Catal. Commun. 2007 , 8 , 2012 – 2016 .
  • Gu , Y. ; Karam , A. ; Jerome , F. ; Barrault , J. Selectivity enhancement of silica-supported sulfonic acid catalysts in water by coating of ionic liquid . Org. Lett. 2007 , 9 , 3145 – 3148 .
  • (a) Polshettiwar , V. ; Varma , R. S. Tandem bis-aldol reaction of ketones: A facile one-pot synthesis of 1,3-dioxanes in aqueous medium . J. Org. Chem. 2007 , 72 , 7420 – 7422 ; (b) Gorrichon , J. P. ; Gaset , A. ; Delmas , M. A one-step synthesis of 1,3-dioxanes from ketones and paraformaldehyde with a cation exchange resin as catalyst . Synthesis 1979 , 219 .
  • Sulmon , P. ; De Kimpe , N. ; Schamp , N. Preparation of α,α-dialkyl-β-halo ketones . Org. Prep. Proc. Int. 1989 , 21 , 91 – 104 .
  • Hao , X. ; Yoshida , A. ; Hoshi , N. Recyclable hafnium(IV) bis(perfluorooctanesulfonyl)amide complex for catalytic Friedel–Crafts acylation and Prins reaction in fluorous biphase system . J. Fluor. Chem. 2007 , 128 , 1396 – 1401 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.