Synthesis of Coumarins Catalyzed by Heterobimetallic Co/Rh Nanoparticles

Kang Hyun Park; Il Gu Jung; Young Keun Chung

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;

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

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References

<A NAME="RU23304ST-1A">1a</A> Musicki B. Periers AM. Piombo L. Laurin P. Klich M. Dupuis-Hamelin C. Lassaigne P. Bonnefoy A. Tetrahedron Lett. 2003, 44: 9259

<A NAME="RU23304ST-1B">1b</A> Gadisseur APA. Breukink-Engbers WGM. van der Meer FJM. van den Besselaar AMH. Sturk A. Rosendaal FR. Arch. Intern. Med. 2003, 163: 2639

<A NAME="RU23304ST-1C">1c</A> Taguchi G. Ubukata T. Hayashida N. Yamamoto H. Okazaki M. Arch. Biochem. Biophys. 2003, 420: 95

<A NAME="RU23304ST-1D">1d</A> Wolzt M. Bostrom SL. Svensson M. Wahlander K. Grind M. Sarich TC. Pathophysiol. Haemo. 2003, 33: 68

<A NAME="RU23304ST-2A">2a</A> Hossain MA. Mihara H. Ueno A. Bioorg. Med. Chem. Lett. 2003, 13: 4305

<A NAME="RU23304ST-2B">2b</A> Choi DW. Lim CW. Sohn SH. Optik 2003, 114: 347

<A NAME="RU23304ST-2C">2c</A> Suzuki AZ. Watanabe T. Kawamoto M. Nishiyama K. Yamashita H. Ishii M. Iwamura M. Furuta T. Org. Lett. 2003, 5: 4867

<A NAME="RU23304ST-2D">2d</A> El-Kemary M. Rettig W. Phys. Chem. Chem. Phys. 2003, 5: 5221

<A NAME="RU23304ST-3A">3a</A> Hepworth JD. Comprehensive Heterocyclic Chemistry Vol. 3: Katrizky AR. Rees CW. Pergamon Press; Oxford: 1984. p.737-883

<A NAME="RU23304ST-3B">3b</A> Stannton J. Comprehensive Organic Chemistry Part 18.2, Vol. 4: Sammes PG. Pergamon Press; Oxford: 1979. p.629-658

<A NAME="RU23304ST-3C">3c</A> Hepworth JD. Gabbutt CD. Heron BM. Comprehensive Heterocyclic Chemistry II Vol. 5: McKillop A. Pergamon Press; Oxford: 1996. Chap. 5.08. p.351-468

<A NAME="RU23304ST-4A">4a</A> Johnson JR. Org. React. 1942, 1: 210

<A NAME="RU23304ST-4B">4b</A> Vijayan KK. Indian J. Heterocycl. Chem. 1998, 8: 1

<A NAME="RU23304ST-4C">4c</A> Mahling JA. Schmidt RR. Liebigs. Ann. 1995, 467

<A NAME="RU23304ST-5A">5a</A> Kakehi A. Ito S. Suga H. Yasuraoka K. Heterocycles 2001, 54: 185

<A NAME="RU23304ST-5B">5b</A> Brufola G. Fringuelli F. Piermatti O. Pizzo F. Heterocycles 1997, 45: 1715

<A NAME="RU23304ST-5C">5c</A> Bojilova A. Nikolova R. Ivanov C. Rodios NA. Terzis A. Raptopoulou CP. Tetrahedron 1996, 52: 12597

<A NAME="RU23304ST-6A">6a</A> Sethna S. Phadke R. Org. React. 1953, 7: 1

<A NAME="RU23304ST-6B">6b</A> Wang LM. Xia JJ. Tian H. Qian CT. Ma Y. Indian J. Chem., Sect. B. 2003, 42: 2097

<A NAME="RU23304ST-6C">6c</A> Laufer MC. Hausmann H. Holderich W. J. Catal. 2003, 218: 315

<A NAME="RU23304ST-6D">6d</A> Bose DS. Rudradas AP. Babu MH. Tetrahedron Lett. 2002, 43: 9195

<A NAME="RU23304ST-7A">7a</A> Ni: Rayabarapu DK. Sambaiah T. Cheng C.-H. Angew. Chem. Int. Ed. 2001, 40: 1286

<A NAME="RU23304ST-7B">7b</A> Rh: Yoneda E. Sugioka T. Hirao K. Zhang S.-W. Takahashi S. J. Chem. Soc., Perkin Trans. 1 1998, 477

<A NAME="RU23304ST-7C">7c</A> Ru: Van T N. Debenedetti S. De Kimpe N. Tetrahedron Lett. 2003, 44: 4199

<A NAME="RU23304ST-7D">7d</A> Pd: Trost BM. Toste FD. J. Am. Chem. Soc. 1996, 108: 6305

<A NAME="RU23304ST-7E">7e</A> Kitamura T. Yamamoto K. Kotani M. Oyamada J. Jia C. Fujiwara Y. Bull. Chem. Soc. Jpn. 2003, 76: 1889

<A NAME="RU23304ST-7F">7f</A> Kadnikov DV. Larock RC. J. Org. Chem. 2003, 68: 9432

<A NAME="RU23304ST-7G">7g</A> An Z. Catellani M. Chiusoli GP. Gazz. Chim. Ital. 1990, 120: 383

<A NAME="RU23304ST-7H">7h</A> Catellani M. Chuisoli GP. Fagnola MC. Solari G. Tetrahedron Lett. 1994, 35: 5919

<A NAME="RU23304ST-7I">7i</A> Catellani M. Chiusoli GP. Fagnola MC. Solari G. Tetrahedron Lett. 1994, 35: 5923

<A NAME="RU23304ST-7J">7j</A> Jia C. Piao D. Oyamada J. Lu W. Kitamura T. Fujiwara Y. Science 2000, 287: 1992

<A NAME="RU23304ST-7K">7k</A> Jia C. Piao D. Kitamura T. Fujiwara Y. J. Org. Chem. 2000, 65: 7516

<A NAME="RU23304ST-8A">8a</A> Roucoux A. Schulz J. Patin H. Chem. Rev. 2002, 102: 3757

<A NAME="RU23304ST-8B">8b</A> Kralik M. Biffis A. J. Mol. Catal. A: Chem. 2001, 177: 113

<A NAME="RU23304ST-8C">8c</A> Thomas JM. Raja R. Chem. Record 2001, 1: 448

<A NAME="RU23304ST-8D">8d</A> Rao CNR. Cheetham AK. J. Mater. Chem. 2001, 11: 2887

<A NAME="RU23304ST-8E">8e</A> Gai PL. Roper R. White MG. Curr. Opin. Solid State Mater. Sci. 2002, 6: 401

<A NAME="RU23304ST-8F">8f</A> Tamura M. Fujihara H. J. Am. Chem. Soc. 2003, 125: 15742

<A NAME="RU23304ST-9A">9a</A> Choi K.-M. Mizugaki T. Ebitani K. Kanrda K. Chem. Lett. 2003, 32: 180

<A NAME="RU23304ST-9B">9b</A> Mallick K. Witcomb MJ. Scurrell MS. Appl. Catal. A: Gen. 2004, 259: 163

<A NAME="RU23304ST-9C">9c</A> Carrettin S. McMorn P. Johnston P. Griffin K. Kiely CJ. Attard GA. Hutchings GJ. Top. Catal. 2004, 27: 131

<A NAME="RU23304ST-9D">9d</A> Arrii S. Morfin F. Renouprez AJ. Rousset JL. J. Am. Chem. Soc. 2004, 126: 1199

<A NAME="RU23304ST-9E">9e</A> Kim Y.-C. Park N.-C. Shin J.-S. Lee SR. Lee YJ. Moon DJ. Catal. Today 2003, 87: 153

<A NAME="RU23304ST-9F">9f</A> Yang C.-m. Kalwei M. Schuth F. Chao K.-j. Appl. Catal. A: Gen. 2003, 254: 289

<A NAME="RU23304ST-9G">9g</A> Lang H. May RA. Iversen BL. Chandler BD.
J. Am. Chem. Soc. 2003, 125: 14832

<A NAME="RU23304ST-10A">10a</A> Chechik V. Crooks RM. J. Am. Chem. Soc. 2000, 122: 1243

<A NAME="RU23304ST-10B">10b</A> Lu P. Teranishi T. Asakura K. Miyake M. Toshima N. J. Phys. Chem. B 1999, 103: 9673

<A NAME="RU23304ST-10C">10c</A> Dupont J. Fonseca GS. Umpierre AP. Fichtner PFP. Teixeira SR. J. Am. Chem. Soc. 2002, 124: 4228

<A NAME="RU23304ST-10D">10d</A> Fonseca GS. Umpierre AP. Fichtner PFP. Teixeira SR. Dupont J. Chem.-Eur. J. 2003, 9: 3263

<A NAME="RU23304ST-10E">10e</A> Yoo JW. Hathcock D. El-Sayed MA. J. Phys. Chem. A 2002, 106: 2049

<A NAME="RU23304ST-10F">10f</A> Adlim M. Abu Bakar M. Liew KY. Ismail J. J. Mol. Catal. A: Chem. 2004, 212: 141

<A NAME="RU23304ST-10G">10g</A> Kidambi S. Dai J. Li J. Bruening ML. J. Am. Chem. Soc. 2004, 126: 2658

<A NAME="RU23304ST-11A">11a</A> Liu Y. Khemtong C. Hu J. Chem. Commun. 2004, 398

<A NAME="RU23304ST-11B">11b</A> Na Y. Park S. Han SB. Han H. Ko S. Chang S. J. Am. Chem. Soc. 2004, 126: 250

<A NAME="RU23304ST-11C">11c</A> Gopidas KR. Whitesell JK. Fox MA. Nano Lett. 2003, 3: 1757

<A NAME="RU23304ST-11D">11d</A> Pittelkow M. Moth-Poulsen K. Boas U. Christensen JB. Langmuir 2003, 19: 7682

<A NAME="RU23304ST-11E">11e</A> Narayanan R. El-Sayed MA. J. Am. Chem. Soc. 2003, 125: 8340

<A NAME="RU23304ST-11F">11f</A> Strimbu L. Liu J. Kaifer AE. Langmuir 2003, 19: 483

<A NAME="RU23304ST-11G">11g</A> Kogan V. Aizenshtat Z. Popovitz-Biro R. Neumann R. Org. Lett. 2002, 4: 3529

<A NAME="RU23304ST-12A">12a</A> Kim S.-W. Son SU. Chung YK. Hyeon T. Chem. Commun. 2001, 2212

<A NAME="RU23304ST-12B">12b</A> Son SU. Lee SI. Chung YK. Kim S.-W. Hyeon T. Org. Lett. 2002, 4: 277

<A NAME="RU23304ST-12C">12c</A> Son SU. Park KH. Chung YK. Org. Lett. 2002, 4: 3983

<A NAME="RU23304ST-12D">12d</A> Park KH. Son SU. Chung YK. Org. Lett. 2002, 4: 4361

<A NAME="RU23304ST-12E">12e</A> Park KH. Son SU. Chung YK. Chem. Commun. 2003, 1898

<A NAME="RU23304ST-13A">13a</A> Sung-Suh HM. Choi JR. Hah HJ. Koo SM. Bae YCJ. Photochem. Photobiol. A: Chem. 2004, 163: 37

<A NAME="RU23304ST-13B">13b</A> Wei H. Wu Y. Lun N. Zhao F. J. Mater. Sci. 2004, 39: 1305

<A NAME="RU23304ST-13C">13c</A> Orlov A. Jefferson DA. Macleod N. Lambert RM. Catal. Lett. 2004, 92: 41

<A NAME="RU23304ST-13D">13d</A> Hong S.-S. Lee MS. Park SS. Lee G.-D. Catal. Today 2003, 87: 99

<A NAME="RU23304ST-13E">13e</A> Hirai T. Nanba M. Komasawa I. J. Colloid Interf. Sci. 2003, 268: 394

<A NAME="RU23304ST-13F">13f</A> Yoshida H. Nishimoto J.-i. Miyashita Y. Ooka C. Komai S.-i. Satsuma A. Hattori T. Chem. Lett. 2003, 32: 1030

<A NAME="RU23304ST-13G">13g</A> Zhang L. Yu JC. Yip HY. Li Q. Kwong KW. Xu A.-W. Wong PK. Langmuir 2003, 19: 10372

<A NAME="RU23304ST-14A">14a</A> Park KH. Kim S.-Y. Chung YK. Org. Lett. 2003, 5: 4967

<A NAME="RU23304ST-14B">14b</A> Park KH. Jung IG. Chung YK. Org. Lett. 2004, 6: 1183

<A NAME="RU23304ST-15">15</A> Kaiser N.-FK. Hallberg A. Larhed M. J. Comb. Chem. 2002, 4: 109