Synthesis of Coumarins Catalyzed by Heterobimetallic Co/Rh Nanoparticles

Kang Hyun Park; Il Gu Jung; Young Keun Chung

doi:10.1055/s-2004-834826

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Synlett 2004(14): 2541-2544
DOI: 10.1055/s-2004-834826

LETTER

Synthesis of Coumarins Catalyzed by Heterobimetallic Co/Rh Nanoparticles

Kang Hyun Park, Il Gu Jung, Young Keun Chung*
School of Chemistry, College of Natural Sciences, Seoul National University, Seoul 151-742, Korea
Fax: +82(2)8890310; e-Mail: ykchung@plaza.snu.ac.kr;

Further Information

Publication History

Received 18 August 2004
Publication Date:
20 October 2004 (online)

Abstract
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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

References

1a Musicki B. Periers AM. Piombo L. Laurin P. Klich M. Dupuis-Hamelin C. Lassaigne P. Bonnefoy A. Tetrahedron Lett. 2003, 44: 9259

Google Scholar
1b Gadisseur APA. Breukink-Engbers WGM. van der Meer FJM. van den Besselaar AMH. Sturk A. Rosendaal FR. Arch. Intern. Med. 2003, 163: 2639

Google Scholar
1c Taguchi G. Ubukata T. Hayashida N. Yamamoto H. Okazaki M. Arch. Biochem. Biophys. 2003, 420: 95

Google Scholar
1d Wolzt M. Bostrom SL. Svensson M. Wahlander K. Grind M. Sarich TC. Pathophysiol. Haemo. 2003, 33: 68

Google Scholar
2a Hossain MA. Mihara H. Ueno A. Bioorg. Med. Chem. Lett. 2003, 13: 4305

Crossref Google Scholar
2b Choi DW. Lim CW. Sohn SH. Optik 2003, 114: 347

Crossref Google Scholar
2c Suzuki AZ. Watanabe T. Kawamoto M. Nishiyama K. Yamashita H. Ishii M. Iwamura M. Furuta T. Org. Lett. 2003, 5: 4867

Crossref Google Scholar
2d El-Kemary M. Rettig W. Phys. Chem. Chem. Phys. 2003, 5: 5221

Crossref Google Scholar
3a Hepworth JD. Comprehensive Heterocyclic Chemistry Vol. 3: Katrizky AR. Rees CW. Pergamon Press; Oxford: 1984. p.737-883

Google Scholar
3b Stannton J. Comprehensive Organic Chemistry Part 18.2, Vol. 4: Sammes PG. Pergamon Press; Oxford: 1979. p.629-658

Google Scholar
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

Google Scholar
4a Johnson JR. Org. React. 1942, 1: 210

Google Scholar
4b Vijayan KK. Indian J. Heterocycl. Chem. 1998, 8: 1

Google Scholar
4c Mahling JA. Schmidt RR. Liebigs. Ann. 1995, 467

Google Scholar
5a Kakehi A. Ito S. Suga H. Yasuraoka K. Heterocycles 2001, 54: 185

Crossref Google Scholar
5b Brufola G. Fringuelli F. Piermatti O. Pizzo F. Heterocycles 1997, 45: 1715

Crossref Google Scholar
5c Bojilova A. Nikolova R. Ivanov C. Rodios NA. Terzis A. Raptopoulou CP. Tetrahedron 1996, 52: 12597

Crossref Google Scholar
6a Sethna S. Phadke R. Org. React. 1953, 7: 1

Crossref Google Scholar
6b Wang LM. Xia JJ. Tian H. Qian CT. Ma Y. Indian J. Chem., Sect. B. 2003, 42: 2097

Crossref Google Scholar
6c Laufer MC. Hausmann H. Holderich W. J. Catal. 2003, 218: 315

Crossref Google Scholar
6d Bose DS. Rudradas AP. Babu MH. Tetrahedron Lett. 2002, 43: 9195

Crossref Google Scholar
7a Ni: Rayabarapu DK. Sambaiah T. Cheng C.-H. Angew. Chem. Int. Ed. 2001, 40: 1286

Google Scholar
7b Rh: Yoneda E. Sugioka T. Hirao K. Zhang S.-W. Takahashi S. J. Chem. Soc., Perkin Trans. 1 1998, 477

Google Scholar
7c Ru: Van T N. Debenedetti S. De Kimpe N. Tetrahedron Lett. 2003, 44: 4199

Google Scholar
7d Pd: Trost BM. Toste FD. J. Am. Chem. Soc. 1996, 108: 6305

Google Scholar
7e Kitamura T. Yamamoto K. Kotani M. Oyamada J. Jia C. Fujiwara Y. Bull. Chem. Soc. Jpn. 2003, 76: 1889

Google Scholar
7f Kadnikov DV. Larock RC. J. Org. Chem. 2003, 68: 9432

Google Scholar
7g An Z. Catellani M. Chiusoli GP. Gazz. Chim. Ital. 1990, 120: 383

Google Scholar
7h Catellani M. Chuisoli GP. Fagnola MC. Solari G. Tetrahedron Lett. 1994, 35: 5919

Google Scholar
7i Catellani M. Chiusoli GP. Fagnola MC. Solari G. Tetrahedron Lett. 1994, 35: 5923

Google Scholar
7j Jia C. Piao D. Oyamada J. Lu W. Kitamura T. Fujiwara Y. Science 2000, 287: 1992

Google Scholar
7k Jia C. Piao D. Kitamura T. Fujiwara Y. J. Org. Chem. 2000, 65: 7516

Google Scholar
8a Roucoux A. Schulz J. Patin H. Chem. Rev. 2002, 102: 3757

Crossref PubMed Google Scholar
8b Kralik M. Biffis A. J. Mol. Catal. A: Chem. 2001, 177: 113

Crossref PubMed Google Scholar
8c Thomas JM. Raja R. Chem. Record 2001, 1: 448

Crossref PubMed Google Scholar
8d Rao CNR. Cheetham AK. J. Mater. Chem. 2001, 11: 2887

Crossref PubMed Google Scholar
8e Gai PL. Roper R. White MG. Curr. Opin. Solid State Mater. Sci. 2002, 6: 401

Crossref PubMed Google Scholar
8f Tamura M. Fujihara H. J. Am. Chem. Soc. 2003, 125: 15742

Crossref PubMed Google Scholar
9a Choi K.-M. Mizugaki T. Ebitani K. Kanrda K. Chem. Lett. 2003, 32: 180

Crossref Google Scholar
9b Mallick K. Witcomb MJ. Scurrell MS. Appl. Catal. A: Gen. 2004, 259: 163

Crossref Google Scholar
9c Carrettin S. McMorn P. Johnston P. Griffin K. Kiely CJ. Attard GA. Hutchings GJ. Top. Catal. 2004, 27: 131

Crossref Google Scholar
9d Arrii S. Morfin F. Renouprez AJ. Rousset JL. J. Am. Chem. Soc. 2004, 126: 1199

Crossref Google Scholar
9e Kim Y.-C. Park N.-C. Shin J.-S. Lee SR. Lee YJ. Moon DJ. Catal. Today 2003, 87: 153

Crossref Google Scholar
9f Yang C.-m. Kalwei M. Schuth F. Chao K.-j. Appl. Catal. A: Gen. 2003, 254: 289

Crossref Google Scholar
9g Lang H. May RA. Iversen BL. Chandler BD.
J. Am. Chem. Soc. 2003, 125: 14832

Crossref Google Scholar
10a Chechik V. Crooks RM. J. Am. Chem. Soc. 2000, 122: 1243

Crossref Google Scholar
10b Lu P. Teranishi T. Asakura K. Miyake M. Toshima N. J. Phys. Chem. B 1999, 103: 9673

Crossref Google Scholar
10c Dupont J. Fonseca GS. Umpierre AP. Fichtner PFP. Teixeira SR. J. Am. Chem. Soc. 2002, 124: 4228

Crossref Google Scholar
10d Fonseca GS. Umpierre AP. Fichtner PFP. Teixeira SR. Dupont J. Chem.-Eur. J. 2003, 9: 3263

Crossref Google Scholar
10e Yoo JW. Hathcock D. El-Sayed MA. J. Phys. Chem. A 2002, 106: 2049

Crossref Google Scholar
10f Adlim M. Abu Bakar M. Liew KY. Ismail J. J. Mol. Catal. A: Chem. 2004, 212: 141

Crossref Google Scholar
10g Kidambi S. Dai J. Li J. Bruening ML. J. Am. Chem. Soc. 2004, 126: 2658

Crossref Google Scholar
11a Liu Y. Khemtong C. Hu J. Chem. Commun. 2004, 398

Crossref Google Scholar
11b Na Y. Park S. Han SB. Han H. Ko S. Chang S. J. Am. Chem. Soc. 2004, 126: 250

Crossref Google Scholar
11c Gopidas KR. Whitesell JK. Fox MA. Nano Lett. 2003, 3: 1757

Crossref Google Scholar
11d Pittelkow M. Moth-Poulsen K. Boas U. Christensen JB. Langmuir 2003, 19: 7682

Crossref Google Scholar
11e Narayanan R. El-Sayed MA. J. Am. Chem. Soc. 2003, 125: 8340

Crossref Google Scholar
11f Strimbu L. Liu J. Kaifer AE. Langmuir 2003, 19: 483

Crossref Google Scholar
11g Kogan V. Aizenshtat Z. Popovitz-Biro R. Neumann R. Org. Lett. 2002, 4: 3529

Crossref Google Scholar
12a Kim S.-W. Son SU. Chung YK. Hyeon T. Chem. Commun. 2001, 2212

Crossref Google Scholar
12b Son SU. Lee SI. Chung YK. Kim S.-W. Hyeon T. Org. Lett. 2002, 4: 277

Crossref Google Scholar
12c Son SU. Park KH. Chung YK. Org. Lett. 2002, 4: 3983

Crossref Google Scholar
12d Park KH. Son SU. Chung YK. Org. Lett. 2002, 4: 4361

Crossref Google Scholar
12e Park KH. Son SU. Chung YK. Chem. Commun. 2003, 1898

Crossref Google Scholar
13a Sung-Suh HM. Choi JR. Hah HJ. Koo SM. Bae YCJ. Photochem. Photobiol. A: Chem. 2004, 163: 37

Crossref Google Scholar
13b Wei H. Wu Y. Lun N. Zhao F. J. Mater. Sci. 2004, 39: 1305

Crossref Google Scholar
13c Orlov A. Jefferson DA. Macleod N. Lambert RM. Catal. Lett. 2004, 92: 41

Crossref Google Scholar
13d Hong S.-S. Lee MS. Park SS. Lee G.-D. Catal. Today 2003, 87: 99

Crossref Google Scholar
13e Hirai T. Nanba M. Komasawa I. J. Colloid Interf. Sci. 2003, 268: 394

Crossref Google Scholar
13f Yoshida H. Nishimoto J.-i. Miyashita Y. Ooka C. Komai S.-i. Satsuma A. Hattori T. Chem. Lett. 2003, 32: 1030

Crossref Google Scholar
13g Zhang L. Yu JC. Yip HY. Li Q. Kwong KW. Xu A.-W. Wong PK. Langmuir 2003, 19: 10372

Crossref Google Scholar
14a Park KH. Kim S.-Y. Chung YK. Org. Lett. 2003, 5: 4967

Crossref Google Scholar
14b Park KH. Jung IG. Chung YK. Org. Lett. 2004, 6: 1183

Crossref Google Scholar
15 Kaiser N.-FK. Hallberg A. Larhed M. J. Comb. Chem. 2002, 4: 109

Crossref PubMed Google Scholar