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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 York
Synthesis 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