Subscribe to RSS
DOI: 10.1055/s-0030-1260060
Molybdenum Hexacarbonyl Mediated Alkoxycarbonylation of Aryl Halides
Publication History
Publication Date:
09 June 2011 (online)

Abstract
Mo(CO)6-mediates the alkoxycarbonylation of aryl halides in their reaction with alcohols to afford arenecarboxylic acid esters. The molybdenum carbonyl complexes act as the catalyst and the source with carbon monoxide. The alkoxycarbonylation proceeds with a small excess of carbon monoxide in the form of Mo(CO)6 and the procedure is simple compared to the conventional method, which uses palladium catalyst under gaseous carbon monoxide. Using this procedure, a variety of carboxylic acid esters were prepared.
Key words
molybdenum - carbonyl complexes - carbonylation - esterification - acylation
- 1a
Schoenberg A.Bartoletti I.Heck RF. J. Org. Chem. 1974, 39: 3318Reference Ris Wihthout Link - 1b
Schoenberg A.Heck RF. J. Org. Chem. 1974, 39: 3327Reference Ris Wihthout Link - 1c
Schoenberg A.Heck RF.
J. Am. Chem. Soc. 1974, 96: 7761Reference Ris Wihthout Link - For palladium-catalyzed carbonylation, see:
- 2a
Colquhoun HM.Thompson DJ.Twigg MV. Carbonylation, Direct Synthesis of Carbonyl Compounds Plenum Press; New York: 1991.Reference Ris Wihthout Link - 2b
Gulevich YV.Bumagin NA.Beletskaya IP. Russ. Chem. Rev. (Engl. Transl.) 1988, 57: 299Reference Ris Wihthout Link - 2c
Beller M.Cornils B.Frohning CD.Kohlpaintner CW. J. Mol. Catal. 1995, 104: 17Reference Ris Wihthout Link - 2d
Stromnova TA.Moiseev II. Russ. Chem. Rev. (Engl. Transl.) 1998, 67: 485Reference Ris Wihthout Link - 2e
Skoda-Földes R.Kollár L. Curr. Org. Chem. 2002, 6: 1097Reference Ris Wihthout Link - 2f
Barnard CFJ. Organometallics 2008, 27: 5402Reference Ris Wihthout Link - 2g
Brennführer A.Neumann H.Beller M. Angew. Chem. Int. Ed. 2009, 48: 4114Reference Ris Wihthout Link - For palladium-catalyzed alkoxycarbonylation, see:
- 3a
Mori M. In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2:Negishi E. Wiley-Interscience; New York: 2000. p.2663Reference Ris Wihthout Link - 3b
Beller M. In Applied Homogeneous Catalysis with Organometallic Compounds 2nd ed., Vol. 1:Cornils B.Herrmann WA. Wiley-VCH; Weinheim: 2002. p.145Reference Ris Wihthout Link - For selected recent examples, see:
- 3c
Neumann H.Brennführer A.Groß P.Riermeier T.Almena J.Beller M. Adv. Synth. Catal. 2006, 348: 1255Reference Ris Wihthout Link - 3d
Jimenez-Rodriguez C.Eastham GR.Cole-Hamilton DJ. Dalton Trans. 2005, 10: 1826Reference Ris Wihthout Link - 3e
Cai MZ.Zhao H.Huang YX. J. Mol. Catal. A: Chem. 2005, 238: 41Reference Ris Wihthout Link - 3f
Iannelli M.Bergamelli F.Kormos CM.Paravisi S.Leadbeater NE. Org. Process Res. Dev. 2009, 13: 634Reference Ris Wihthout Link - 3g
Salvadori J.Balducci E.Zaza S.Petricci E.Taddei M. J. Org. Chem. 2010, 75: 1841Reference Ris Wihthout Link - For a review, see:
- 4a
Morimoto T.Kakiuchi K. Angew. Chem. Int. Ed. 2004, 43: 5580Reference Ris Wihthout Link - For using aldehyde as the substitute for CO gas, see:
- 4b
Morimoto T.Fujioka M.Fuji K.Tsutsumi K.Kakiuchi K. Chem. Lett. 2003, 32: 154Reference Ris Wihthout Link - 4c
Morimoto T.Fujioka M.Fuji K.Tsutsumi K.Kakiuchi K. J. Organomet. Chem. 2007, 692: 625Reference Ris Wihthout Link - For using formamide, see:
- 4d
Wan YQ.Alterman M.Larhed M.Hallberg A. J. Comb. Chem. 2003, 5: 82Reference Ris Wihthout Link - For using DMF, see:
- 4e
Hosoi K.Nozaki K.Hiyama T. Org. Lett. 2002, 4: 2849Reference Ris Wihthout Link - 4f
Wan YQ.Alterman M.Larhed M.Hallberg A. J. Org. Chem. 2002, 67: 6232Reference Ris Wihthout Link - 4g
Ju J.Jeong M.Moon J.Jung HM.Lee S. Org. Lett. 2007, 9: 4615Reference Ris Wihthout Link - 4h
Tambade PJ.Patil YP.Bhanushali MJ.Bhanage BM. Tetrahedron Lett. 2008, 49: 2221Reference Ris Wihthout Link - For using CHCl3, see:
- 4i
Grushin VV.Alper H. Organometallics 1993, 12: 3846Reference Ris Wihthout Link - For using acetic formic anhydride, see:
- 4j
Cacchi S.Fabrizi G.Goggiamani A. Org. Lett. 2003, 5: 4269Reference Ris Wihthout Link - For using AcCl, see:
- 4k
Hermange P.Lindhardt AT.Taaning RH.Bjerglund K.Lupp D.Skrydstrup T. J. Am. Chem. Soc. 2011, 133: 6061Reference Ris Wihthout Link - 5a
Kaiser N.-FK.Hallberg A.Larhed M. J. Comb. Chem. 2002, 4: 109Reference Ris Wihthout Link - 5b
Wan Y.Alterman M.Larhed M.Hallberg A. J. Org. Chem. 2002, 67: 6232Reference Ris Wihthout Link - 5c
Wannbeg J.Larhed M. J. Org. Chem. 2003, 68: 5750Reference Ris Wihthout Link - 5d
Wan Y.Alterman M.Larhed M.Hallberg A. J. Comb. Chem. 2003, 5: 82Reference Ris Wihthout Link - 6
Ren W.Yamane M. J. Org. Chem. 2010, 75: 8410 - 7 Recently, Roberts and co-workers
reported the Mo-mediated carbonylation of aryl halides with various
nucleophiles under microwave irradiation. They used Mo(CO)6 (1.0 equiv)
with respect to the aryl halides, see:
Roberts B.Liptrot D.Alcaraz L.Luker T.Stocks MJ. Org. Lett. 2010, 12: 4280 - 9
Zippi EM. Synth. Commun. 1994, 24: 2515 - 10
Khan KM.Maharvi GM.Hayat S. .Choudhary MI. . Tetrahedron 2003, 59: 5549 - 11
Arrowsmith GB.Jeffery GH.Vogel AI. J. Chem. Soc. 1965, 2072 - 12
Wiles C.Watts P.Haswell SJ. Tetrahedron Lett. 2006, 47: 5261 - 13
Ramesh C.Nakamura R.Kubota Y.Miwa M.Sugi Y. Synthesis 2003, 501 - 14
Liu Z.Larock RC. J. Org. Chem. 2006, 71: 3198 - 15
Watson DA.Fan X.Buchwald SL. J. Org. Chem. 2008, 73: 7096 - 16
Urano T.Kitamura A.Sakuragi H.Tokumaru K. Chem. Lett. 1983, 867 - 17
Endo T.Saotome Y.Okawara M. J. Am. Chem. Soc. 1984, 106: 1124 - 18
Shintou T.Fukumoto K.Mukaiyama T. Bull. Chem. Soc. Jpn. 2004, 77: 1569 - 19
Chan W.-C.Mooney JA.Windle AH. Mol. Cryst. Liq. Cryst. 1989, 174: 75 - 20
Silverman SK.Foote CS. J. Am. Chem. Soc. 1991, 113: 7672 - 21
Chen CT.Munot YS. J. Org. Chem. 2005, 70: 8625 - 22
Ishihara K.Kubota M.Kurihara H.Yamamoto H. J. Org. Chem. 1996, 61: 4560 - 23
Doering WE.Levy LK. J. Am. Chem. Soc. 1955, 77: 509 - 24
Kanoh S.Nishimura T.Naka M.Motoi M. Tetrahedron 2002, 58: 7065 - 25
Yamazaki S. Org. Lett. 1999, 1: 212
References
The additive Et4NCl was sometimes effective in the carbamoylation of aryl halides. See ref. 6.