Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans

ACS Combinatorial Science

Volumn 13, Issue 3, 2011, Pages 272-279

  Cho, Chul Hee ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

carboalkoxylation; cyclocarbonylation; furan; iodocyclization; nucleophile

Indexed keywords

ESTER; FURAN DERIVATIVE; LACTONE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; ESTERS; FURANS; LACTONES; PALLADIUM;

EID: 79955857256     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co100088q     Document Type: Article

References (36)

1. Lipshutz, B. H. Five-Membered Heteroaromatic Rings as Intermediates in Organic Synthesis Chem. Rev. 1986, 86, 795-819
2. Keay, B. A. Synthesis of Multi-substituted Furan Rings: The Role of Silicon Chem. Soc. Rev. 1999, 28, 209-215
3. Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Regioselective Syntheses of Substituted Furans Tetrahedron 1998, 54, 1955-2020 (Pubitemid 28067942)
4. 3-Catalyzed Synthesis of Highly Substituted Furans from 2-(1-Alkynyl)-2-alken-1-ones J. Am. Chem. Soc. 2004, 126, 11164-11165 (Pubitemid 39232107)
5. Yao, T.; Zhang, X.; Larock, R. C. Synthesis of Highly Substituted Furans by the Electrophile-Induced Coupling of 2-(1-Alkynyl)-2-alken-1-ones and Nucleophiles J. Org. Chem. 2005, 70, 7679-7685 (Pubitemid 41319750)
6. Brown, R. C. D. Developments in Furan Syntheses Angew. Chem., Int. Ed. 2005, 44, 850-852 (Pubitemid 40239011)
7. Babudri, F.; Cicco, S. R.; Farinola, G. M.; Lopez, L. C.; Naso, F.; Pinto, V. A Novel Cyclization Reaction between 2,3-Bis(trimethylsilyl)buta-1,3- diene and Acyl Chlorides with Straightforward Formation of Polysubstituted Furans Chem. Commun. 2007, 3756-3758 (Pubitemid 47404165)
8. Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kel?in, A. V.; Gevorgyan, V. Metal-Catalyzed 1,2-Shift of Diverse Migrating Groups in Allenyl Systems as a New Paradigm toward Densely Functionalized Heterocycles J. Am. Chem. Soc. 2008, 130, 1440-1452 (Pubitemid 351171023)
9. Sydnes, L. K.; Holmelid, B.; Sengee, M.; Hanstein, M. New Regiospecific Synthesis of Tri- and Tetra-Substituted Furans J. Org. Chem. 2009, 74, 3430-3443
10. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Transition Metal-Catalyzed Carbocyclizations in Organic Synthesis Chem. Rev. 1996, 96, 635-662 (Pubitemid 126649161)
11. Brennführer, A.; Neumann, H.; Beller, M. Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds Angew. Chem., Int. Ed. 2009, 48, 4114-4133
12. Schoenberg, A.; Heck, R. F. Palladium-Catalyzed Formylation of Aryl, Heterocyclic, and Vinylic Halides J. Am. Chem. Soc. 1974, 96, 7761-7764
13. Kormos, C. M.; Leadbeater, N. E. Microwave-Promoted Hydroxycarbonylation in Water Using Gaseous Carbon Monoxide and Pre-Pressurized Reaction Vessels Synlett 2006, 1663-1666 (Pubitemid 44106237)
14. El Ali, B.; Okuro, K.; Vasapollo, G.; Alper, H. Regioselective Palladium(II)-Catalyzed Synthesis of Five- or Seven-Membered Ring Lactones and Five-, Six- or Seven-Membered Ring Lactams by Cyclocarbonylation Methodology J. Am. Chem. Soc. 1996, 118, 4264-4270
15. Negishi, E.; Copéret, C.; Ma, S.; Mita, T.; Sugihara, T.; Tour, J. M. Palladium-Catalyzed Carbonylative Cyclization of 1-Iodo-2-alkenylbenzenes J. Am. Chem. Soc. 1996, 118, 5904-5918 (Pubitemid 26236811)
16. Kreimerman, S.; Ryu, I.; Minakata, S.; Komatsu, M. Lactone Synthesis Based on Atom Transfer Carbonylation Org. Lett. 2000, 2, 389-391
17. Schiller, R.; Pour, M.; Fáková, H.; Kuneš, J.; Císa?ová, I. Neighboring Group Effect in Pd-Catalyzed Carbonylation Terminated by Lactonization: A Need for a Protective Group and/or DMF J. Org. Chem. 2004, 69, 6761-6765 (Pubitemid 39304809)
18. Fernandes, T. A.; Carvalho, R. C. C.; Gonc̃alves, T. M. D.; da Silva, A. J. M.; Costa, P. R. R. A Tandem Palladium-Catalyzed Heck-Lactonization through the Reaction of ortho -Iodophenols with β-Substituted Acrylates: Synthesis of 4,6-Substituted Coumarins Tetrahedron Lett. 2008, 49, 3322-3325
19. Kadnikov, D. V.; Larock, R. C. Synthesis of Coumarins via Palladium-Catalyzed Carbonylative Annulation of Internal Alkynes by o -Iodophenols Org. Lett. 2000, 2, 3643-3646
20. Kadnikov, D. V.; Larock, R. C. Palladium-Catalyzed Carbonylative Annulation of Internal Alkynes: Synthesis of 3,4-Disubstituted Coumarins J. Org. Chem. 2003, 68, 9423-9432 (Pubitemid 37456515)
21. Yao, T.; Yue, D.; Larock, R. C. An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization J. Org. Chem. 2005, 70, 9985-9989 (Pubitemid 41689164)
22. Cho, C.-H.; Larock, R. C. A Convenient Synthetic Route to Furan Esters and Lactones by Palladium-Catalyzed Carboalkoxylation or Cyclocarbonylation of Hydroxyl-Substituted 3-Iodofurans Tetrahedron Lett. 2010, 51, 3417-3421
23. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis Angew. Chem., Int. Ed. 2005, 44, 4442-4489 (Pubitemid 41026385)
24. Cho, C.-H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. Parallel Synthesis of a Multi-Substituted Benzo[b]furan Library J. Comb. Chem. 2008, 10, 941-947
25. Waldo, J. P.; Mehta, S.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. Solution Phase Synthesis of a Diverse Library of Highly Substituted Isoxazoles J. Comb. Chem. 2008, 10, 658-663
26. Cho, C.-H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. Solution-Phase Parallel Synthesis of a Multi-substituted Benzo[b]thiophene Library J. Comb. Chem. 2009, 11, 900-906
27. Worlikar, S. A.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. Highly Substituted Indole Library Synthesis by Palladium-Catalyzed Coupling Reactions in Solution and on a Solid Support J. Comb. Chem. 2009, 11, 875-879
28. Cho, C.-H.; Jung, D.-I.; Larock, R. C. A New Approach to Desketoraloxifene Analogs from Oxygen-Bearing 3-Iodobenzo[b]thiophenes Prepared via Iodocyclization Tetrahedron Lett. 2010, 51, 6485-6488
29. Cho, C.-H.; Neuenswander, B.; Larock, R. C. Diverse Methyl Sulfone-Containing Benzo[b]thiophene Library via Iodocyclization and Palladium-Catalyzed Coupling J. Comb. Chem. 2010, 12, 278-285
30. Suzuki, A. Carbon-Carbon Bonding Made Easy Chem. Commun. 2005, 4759-4763 (Pubitemid 41503185)
31. Sonogashira, K.; Tohda, Y.; Hagihara, N. A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes and Bromopyridines Tetrahedron Lett. 1975, 16, 4467-4470
32. Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation Top. Curr. Chem. 2002, 219, 131-209
33. Hartwig, J. F. Carbon-Heteroatom Bond Formation Catalysed by Organometallic Complexes Nature 2008, 455, 314-322
34. Grese, T. A.; Cho, S.; Finley, D. R.; Godfrey, A. G.; Jones, C. D.; Lugar, C. W.; Martin, M. J.; Matsumoto, K.; Pennington, L. D.; Winter, M. A.; Adrian, M. D.; Cole, H. W.; Magee, D. E.; Phillips, D. L.; Rowley, E. R.; Short, L. L.; Glasebrook, A. L.; Bryant, H. U. Structure-Activity Relationships of Selective Estrogen Receptor Modulators: Modifications to the 2-Arylbenzothiophene Core of Raloxifene J. Med. Chem. 1997, 40, 146-167 (Pubitemid 27045072)
35. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings Adv. Drug Delivery Rev. 1997, 23, 3-25 (Pubitemid 27046991)
36. 2 in an Aqueous Medium Synlett 2005, 1263-1266 (Pubitemid 40755304)