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Synlett 2004(14): 2541-2544
DOI: 10.1055/s-2004-834826
DOI: 10.1055/s-2004-834826
LETTER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Coumarins Catalyzed by Heterobimetallic Co/Rh Nanoparticles
Further Information
Received
18 August 2004
Publication Date:
20 October 2004 (online)
Publication History
Publication Date:
20 October 2004 (online)
Abstract
Described here is the use of cobalt/rhodium (Co2Rh2) heterobimetallic nanoparticles in the catalytic synthesis of coumarins via cyclocarbonylation of alkynes with 2-iodophenol under 1 atm of carbon monoxide and reaction of phenol with propiolic esters.
Key words
coumarins - nanoparticles - heterobimetallic - cyclocarbonylation - catalysis
- 1a
Musicki B.Periers AM.Piombo L.Laurin P.Klich M.Dupuis-Hamelin C.Lassaigne P.Bonnefoy A. Tetrahedron Lett. 2003, 44: 9259 - 1b
Gadisseur APA.Breukink-Engbers WGM.van der Meer FJM.van den Besselaar AMH.Sturk A.Rosendaal FR. Arch. Intern. Med. 2003, 163: 2639 - 1c
Taguchi G.Ubukata T.Hayashida N.Yamamoto H.Okazaki M. Arch. Biochem. Biophys. 2003, 420: 95 - 1d
Wolzt M.Bostrom SL.Svensson M.Wahlander K.Grind M.Sarich TC. Pathophysiol. Haemo. 2003, 33: 68 - 2a
Hossain MA.Mihara H.Ueno A. Bioorg. Med. Chem. Lett. 2003, 13: 4305 - 2b
Choi DW.Lim CW.Sohn SH. Optik 2003, 114: 347 - 2c
Suzuki AZ.Watanabe T.Kawamoto M.Nishiyama K.Yamashita H.Ishii M.Iwamura M.Furuta T. Org. Lett. 2003, 5: 4867 - 2d
El-Kemary M.Rettig W. Phys. Chem. Chem. Phys. 2003, 5: 5221 - 3a
Hepworth JD. Comprehensive Heterocyclic Chemistry Vol. 3:Katrizky AR.Rees CW. Pergamon Press; Oxford: 1984. p.737-883 - 3b
Stannton J. Comprehensive Organic Chemistry Part 18.2, Vol. 4:Sammes PG. Pergamon Press; Oxford: 1979. p.629-658 - 3c
Hepworth JD.Gabbutt CD.Heron BM. Comprehensive Heterocyclic Chemistry II Vol. 5:McKillop A. Pergamon Press; Oxford: 1996. Chap. 5.08. p.351-468 - 4a
Johnson JR. Org. React. 1942, 1: 210 - 4b
Vijayan KK. Indian J. Heterocycl. Chem. 1998, 8: 1 - 4c
Mahling JA.Schmidt RR. Liebigs. Ann. 1995, 467 - 5a
Kakehi A.Ito S.Suga H.Yasuraoka K. Heterocycles 2001, 54: 185 - 5b
Brufola G.Fringuelli F.Piermatti O.Pizzo F. Heterocycles 1997, 45: 1715 - 5c
Bojilova A.Nikolova R.Ivanov C.Rodios NA.Terzis A.Raptopoulou CP. Tetrahedron 1996, 52: 12597 - 6a
Sethna S.Phadke R. Org. React. 1953, 7: 1 - 6b
Wang LM.Xia JJ.Tian H.Qian CT.Ma Y. Indian J. Chem., Sect. B. 2003, 42: 2097 - 6c
Laufer MC.Hausmann H.Holderich W. J. Catal. 2003, 218: 315 - 6d
Bose DS.Rudradas AP.Babu MH. Tetrahedron Lett. 2002, 43: 9195 - 7a Ni:
Rayabarapu DK.Sambaiah T.Cheng C.-H. Angew. Chem. Int. Ed. 2001, 40: 1286 - 7b Rh:
Yoneda E.Sugioka T.Hirao K.Zhang S.-W.Takahashi S. J. Chem. Soc., Perkin Trans. 1 1998, 477 - 7c Ru:
Van T N.Debenedetti S.De Kimpe N. Tetrahedron Lett. 2003, 44: 4199 - 7d Pd:
Trost BM.Toste FD. J. Am. Chem. Soc. 1996, 108: 6305 - 7e
Kitamura T.Yamamoto K.Kotani M.Oyamada J.Jia C.Fujiwara Y. Bull. Chem. Soc. Jpn. 2003, 76: 1889 - 7f
Kadnikov DV.Larock RC. J. Org. Chem. 2003, 68: 9432 - 7g
An Z.Catellani M.Chiusoli GP. Gazz. Chim. Ital. 1990, 120: 383 - 7h
Catellani M.Chuisoli GP.Fagnola MC.Solari G. Tetrahedron Lett. 1994, 35: 5919 - 7i
Catellani M.Chiusoli GP.Fagnola MC.Solari G. Tetrahedron Lett. 1994, 35: 5923 - 7j
Jia C.Piao D.Oyamada J.Lu W.Kitamura T.Fujiwara Y. Science 2000, 287: 1992 - 7k
Jia C.Piao D.Kitamura T.Fujiwara Y. J. Org. Chem. 2000, 65: 7516 - 8a
Roucoux A.Schulz J.Patin H. Chem. Rev. 2002, 102: 3757 - 8b
Kralik M.Biffis A. J. Mol. Catal. A: Chem. 2001, 177: 113 - 8c
Thomas JM.Raja R. Chem. Record 2001, 1: 448 - 8d
Rao CNR.Cheetham AK. J. Mater. Chem. 2001, 11: 2887 - 8e
Gai PL.Roper R.White MG. Curr. Opin. Solid State Mater. Sci. 2002, 6: 401 - 8f
Tamura M.Fujihara H. J. Am. Chem. Soc. 2003, 125: 15742 - 9a
Choi K.-M.Mizugaki T.Ebitani K.Kanrda K. Chem. Lett. 2003, 32: 180 - 9b
Mallick K.Witcomb MJ.Scurrell MS. Appl. Catal. A: Gen. 2004, 259: 163 - 9c
Carrettin S.McMorn P.Johnston P.Griffin K.Kiely CJ.Attard GA.Hutchings GJ. Top. Catal. 2004, 27: 131 - 9d
Arrii S.Morfin F.Renouprez AJ.Rousset JL. J. Am. Chem. Soc. 2004, 126: 1199 - 9e
Kim Y.-C.Park N.-C.Shin J.-S.Lee SR.Lee YJ.Moon DJ. Catal. Today 2003, 87: 153 - 9f
Yang C.-m.Kalwei M.Schuth F.Chao K.-j. Appl. Catal. A: Gen. 2003, 254: 289 - 9g
Lang H.May RA.Iversen BL.Chandler BD.
J. Am. Chem. Soc. 2003, 125: 14832 - 10a
Chechik V.Crooks RM. J. Am. Chem. Soc. 2000, 122: 1243 - 10b
Lu P.Teranishi T.Asakura K.Miyake M.Toshima N. J. Phys. Chem. B 1999, 103: 9673 - 10c
Dupont J.Fonseca GS.Umpierre AP.Fichtner PFP.Teixeira SR. J. Am. Chem. Soc. 2002, 124: 4228 - 10d
Fonseca GS.Umpierre AP.Fichtner PFP.Teixeira SR.Dupont J. Chem.-Eur. J. 2003, 9: 3263 - 10e
Yoo JW.Hathcock D.El-Sayed MA. J. Phys. Chem. A 2002, 106: 2049 - 10f
Adlim M.Abu Bakar M.Liew KY.Ismail J. J. Mol. Catal. A: Chem. 2004, 212: 141 - 10g
Kidambi S.Dai J.Li J.Bruening ML. J. Am. Chem. Soc. 2004, 126: 2658 - 11a
Liu Y.Khemtong C.Hu J. Chem. Commun. 2004, 398 - 11b
Na Y.Park S.Han SB.Han H.Ko S.Chang S. J. Am. Chem. Soc. 2004, 126: 250 - 11c
Gopidas KR.Whitesell JK.Fox MA. Nano Lett. 2003, 3: 1757 - 11d
Pittelkow M.Moth-Poulsen K.Boas U.Christensen JB. Langmuir 2003, 19: 7682 - 11e
Narayanan R.El-Sayed MA. J. Am. Chem. Soc. 2003, 125: 8340 - 11f
Strimbu L.Liu J.Kaifer AE. Langmuir 2003, 19: 483 - 11g
Kogan V.Aizenshtat Z.Popovitz-Biro R.Neumann R. Org. Lett. 2002, 4: 3529 - 12a
Kim S.-W.Son SU.Chung YK.Hyeon T. Chem. Commun. 2001, 2212 - 12b
Son SU.Lee SI.Chung YK.Kim S.-W.Hyeon T. Org. Lett. 2002, 4: 277 - 12c
Son SU.Park KH.Chung YK. Org. Lett. 2002, 4: 3983 - 12d
Park KH.Son SU.Chung YK. Org. Lett. 2002, 4: 4361 - 12e
Park KH.Son SU.Chung YK. Chem. Commun. 2003, 1898 - 13a
Sung-Suh HM.Choi JR.Hah HJ.Koo SM.Bae YCJ. Photochem. Photobiol. A: Chem. 2004, 163: 37 - 13b
Wei H.Wu Y.Lun N.Zhao F. J. Mater. Sci. 2004, 39: 1305 - 13c
Orlov A.Jefferson DA.Macleod N.Lambert RM. Catal. Lett. 2004, 92: 41 - 13d
Hong S.-S.Lee MS.Park SS.Lee G.-D. Catal. Today 2003, 87: 99 - 13e
Hirai T.Nanba M.Komasawa I. J. Colloid Interf. Sci. 2003, 268: 394 - 13f
Yoshida H.Nishimoto J.-i.Miyashita Y.Ooka C.Komai S.-i.Satsuma A.Hattori T. Chem. Lett. 2003, 32: 1030 - 13g
Zhang L.Yu JC.Yip HY.Li Q.Kwong KW.Xu A.-W.Wong PK. Langmuir 2003, 19: 10372 - 14a
Park KH.Kim S.-Y.Chung YK. Org. Lett. 2003, 5: 4967 - 14b
Park KH.Jung IG.Chung YK. Org. Lett. 2004, 6: 1183 - 15
Kaiser N.-FK.Hallberg A.Larhed M. J. Comb. Chem. 2002, 4: 109