Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 21
658
Views
52
CrossRef citations to date
0
Altmetric
Original Articles

Efficient DMF‐Catalyzed Coupling of Epoxides with CO2 under Solvent‐Free Conditions to Afford Cyclic Carbonates

&
Pages 3141-3148 | Received 09 Mar 2006, Published online: 24 Nov 2006

References

  • Inoue , S. 1982 . Organic and Bio‐organic Chemistry of Carbon Dioxide New York : John Wiley & Sons .
  • Darensbourg , D. J. and Holtcamp , M. W. 1996 . Catalysis for the reactions of epoxides and carbon dioxide . Coord. Chem. Rev. , 153 : 155
  • Leitner , W. 1996 . The coordination chemistry of carbon dioxide and its relevance for catalysis: A critical survey . Coord. Chem. Rev. , 153 : 257
  • Gibson , D. H. 1996 . The organometallic chemistry of carbon dioxide . Chem. Rev. , 96 : 2063
  • Trost , B. M. and Angle , S. F. 1985 . Palladium‐mediated vicinal cleavage of allyl epoxides with retention of stereochemistry: A cis hydroxylation equivalent . J. Am. Chem. Soc. , 107 : 6123
  • Fujinami , T. , Suzuki , T. , Kamiya , M. , Fukukawa , S. and Sakai , S. 1985 . Palladium catalyzed reaction of butadiene monoxide with carbon dioxide . Chem. Lett. , : 199
  • Pfaendler , H. R. and Mueller , F. X. 1992 . A simple preparation of enol ether lipids . Synthesis , : 350
  • Minami , T. and Hanaoka , M. 1994 . Synthesis of α,β‐unsaturated aldehydes through palladium‐catalyzed regioselective hydrogen migration . Tetrahedron Lett. , 35 : 9425
  • Mizojiri , R. and Kobayashi , Y. 1995 . Regioselectivity in the nickel‐catalysed coupling of cyclic carbonates of but‐3‐ene‐1,2‐diols with organoborates . J. Chem. Soc., Perkin Trans. 1. , : 2073
  • Matsumoto , K. , Fuwa , S. and Kitajima , H. 1995 . Enzyme‐mediated enantioselective hydrolysis of cyclic carbonates . Tetrahedron Lett. , 36 : 6499
  • Streicher , H. , Geyer , A. and Schmidt , R. R. 1996 . C‐disaccharides of ketoses . Chem. Eur. J. , 2 : 502
  • Chang , H.‐T. and Sharpless , K. B. 1996 . A practical route to enantiopure 1,2‐aminoalcohols . Tetrahedron Lett. , 37 : 3219
  • Schultze , L. M. , Chapman , H. H. , Dubree , N. J. P. , Jones , R. J. , Kent , K. M. , Lee , T. T. , Louie , M. S. , Postich , M. J. , Prisbe , E. J. , Rohloff , J. C. and Yu , R. H. 1998 . Practical synthesis of anti‐HIV drug, PMPA . Tetrahedron Lett. , 39 : 1853
  • Mannafov , T. G. , Berdnikov , E. A. and Samuilov , Y. D. 2001 . Reactions of dichlorocarbene and arenesulfenyl chlorides with 3,4‐epoxy‐1‐butene and vinylethylene carbonate . Russ. J. Org. Chem. , 37 : 339
  • Bhanage , B. M. , Fujita , S.‐I. , He , Y. , Ikushima , Y. , Shirai , M. , Torii , K. and Arai , M. 2002 . Concurrent synthesis of dimethyl carbonate and ethylene glycol via transesterification of ethylene carbonate and methanol using smectite catalysts containing Mg and/or Ni . Catal. Lett. , 83 : 137
  • Clements , J. H. 2003 . Reactive applications of cyclic alkylene carbonates . Ind. Eng. Chem. Res. , 42 : 663
  • Webster , D. C. 2003 . Cyclic carbonate functional polymers and their applications . Progr. Org. Coat. , 47 : 77
  • Yamaguchi , K. , Ebitani , K. , Yoshida , T. , Yoshida , H. and Kaneda , K. 1999 . Mg‐Al mixed oxides as highly active acid–base catalysts for cycloaddition of carbon dioxide to epoxides . J. Am. Chem. Soc. , 121 : 4526
  • Kim , H. S. , Kim , J. J. , Lee , B. G. , Jung , O. S. , Jang , H. G. and Kang , S. O. 2000 . Isolation of a pyridinium alkoxy ion bridged dimeric zinc complex for the coupling reactions of CO2 and epoxides . Angew. Chem. Int. Ed. , 39 : 4096
  • Darensbourg , D. J. , Wildeson , J. R. , Yarbrough , J. C. and Reibenspies , J. H. 2000 . bis‐2,6‐Difluorophenoxide dimeric complexes of zinc and cadmium and their phosphine adducts: Lessons learned relative to carbon dioxide/cyclohexene oxide alternating copolymerization processes catalyzed by zinc phenoxides . J. Am. Chem. Soc. , 122 : 12487
  • Allen , S. D. , Moore , D. R. , Lobkovsky , E. B. and Coates , G. W. 2002 . High‐activity, single‐site catalysts for the alternating copolymerization of CO2 and propylene oxide . J. Am. Chem. Soc. , 124 : 14284
  • Kim , H. S. , Kim , J. J. , Kwon , H. N. , Chung , M. J. , Lee , B. G. and Jang , H. G. 2002 . Well‐defined highly active heterogeneous catalyst system for the coupling reactions of carbon dioxide and epoxides . J. Catal. , 205 : 226
  • Huang , J.‐W. and Shi , M. 2003 . Chemical fixation of carbon dioxide by NaI/PPh3/PhOH . J. Org. Chem. , 68 : 6705
  • Kim , H. S. , Kim , J. J. , Lee , S. D. , Lah , M. S. , Moon , D. and Jang , H. G. 2003 . New mechanistic insight into the coupling reactions of CO2 and epoxides in the presence of zinc complexes . Chem. Eur. J. , 9 : 678
  • Calo , V. , Nacci , A. , Monopoli , A. and Fanizzi , A. 2002 . Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts . Org. Lett. , 4 : 2561
  • Kawanami , H. , Sasaki , A. , Matsui , K. and Ikushima , Y. 2003 . A rapid and effective synthesis of propylene carbonate using a supercritical CO2–ionic liquid system . Chem. Commun. , : 896
  • Sun , J. , Fujita , S. and Arai , M. 2005 . Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids . J. Organomet. Chem. , 690 : 3490
  • Kruper , W. J. and Dellar , D. V. 1995 . Catalytic formation of cyclic carbonates from epoxides and CO2 with chromium metalloporphyrinates . J. Org. Chem. , 60 : 725
  • Sivakumar , T. , Seshadri , R. and Gopalakrishnan , J. 2001 . Bridging the Ruddlesden–Popper and the aurivillius phases: Synthesis and structure of a novel series of layered perovskite oxides, (BiO)LnTiO4 (Ln=La, Nd, Sm) . J. Am. Chem. Soc. , 123 : 11496
  • Li , F. , Xia , C. , Xu , L. , Sun , W. and Chen , G. 2003 . A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides . Chem. Commun. , : 2042
  • Shen , Y.‐M. , Duan , W.‐L. and Shi , M. 2003 . Chemical fixation of carbon dioxide catalyzed by binaphthyldiamino Zn, Cu, and Co Salen‐type complexes . J. Org. Chem. , 68 : 1559
  • Shen , Y.‐M. , Duan , W.‐L. and Shi , M. 2003 . Phenol and organic bases co‐catalyzed chemical fixation of carbon dioxide with terminal epoxides to form cyclic carbonates . Adv. Synth. Catal. , 345 : 337
  • Yoshida , M. and Ihara , M. 2004 . Novel methodologies for the synthesis of cyclic carbonates . Chem. Eur. J. , 10 : 2886
  • Jiang , J.‐L. , Gao , F. , Hua , R. and Qiu , X. 2005 . Re(CO)5Br‐catalyzed coupling of epoxides with CO2 affording cyclic carbonates under solvent‐free conditions . J. Org. Chem. , 70 : 381
  • Man , M. L. , Lam , K. C. , Sit , W. N. , Ng , S. M. , Zhou , Z. , Lin , Z. and Lau , C. P. 2006 . Synthesis of heterobimetallic Ru‐Mn complexes and the coupling reactions of epoxides with carbon dioxide catalyzed by these complexes . Chem. Eur. J. , 12 : 1004
  • Dalko , P. I. and Moisan , L. 2001 . Enantioselective organocatalysis . Angew. Chem. Int. Ed. , 40 : 3726
  • Paras , N. A. and MacMillian , D. W. C. 2001 . New strategies in organic catalysis: The first enantioselective organocatalytic Friedel–Crafts alkylation . J. Am. Chem. Soc. , 123 : 4370 and references therein
  • McDaid , P. , Chen , Y. and Deng , L. 2002 . A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst . Angew. Chem. Int. Ed. , 41 : 338
  • Papageorgiou , C. D. , Ley , S. V. and Gaunt , M. J. 2003 . Organic‐catalyst‐mediated cyclopropanation reaction . Angew. Chem. Int. Ed. , 42 : 828
  • Benaglia , M. , Puglisi , A. and Cozzi , F. 2003 . Polymer‐supported organic catalysts . Chem. Rev. , 103 : 3401
  • Dalko , P. I. and Moisan , L. 2004 . In the golden age of organocatalysis . Angew. Chem. Int. Ed. , 43 : 5138
  • Westermann , B. and Neuhaus , C. 2005 . Dihydroxyacetone in amino acid catalyzed Mannich‐type reactions . Angew. Chem. Int. Ed. , L44 : 4077
  • Casas , J. , Engqvist , M. , Ibarahem , I. , Kaynak , B. and Cordova , A. 2005 . Direct amino acid catalyzed asymmetric synthesis of polyketide sugars . Angew. Chem. Int. Ed. , 44 : 1343
  • Kawanami , H. and Ikushima , Y. 2000 . Chemical fixation of carbon dioxide to styrene carbonate under supercritical conditions with DMF in the absence of any additional catalysts . Chem. Commun. , : 2089

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.