Synthesis of oxazole and furan derivatives via Rh₂(OAc)₄-catalyzed C≡X bond insertion of cyclic 2-diazo-1,3-diketones with nitriles and arylacetylenes

References

• (a) Richard, C.; Frank, S.; Paul, H.; Björn, Å. Direct Preparation of 4-Carboethoxy-1,3-Oxazoles. Tetrahedron Lett. 1991, 32, 17–20. (b) Richard, D. C.; Mark, T.; Anthony, R. G.; Paul, H.; Björn, Å. Rhodium-Catalyzed Heterocycloaddition Route to 1,3-Oxazoles as Building Blocks in Natural Products Synthesis. Tetrahedron. 1993, 49, 5445–5449. (c) Padwa, A.; Straub, C. S. Synthesis of Furo[3,4-c]Furans Using a Rhodium(II)-Catalyzed Cyclization/Diels − Alder Cycloaddition Sequence. J. Org. Chem. 2003, 68, 227–239. (d) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles. Chem. Rev. 2013, 113, 3084–3213.
   Web of Science ®Google Scholar
• (a) Senadi, G. C.; Hu, W. P.; Hsiao, J. S.; Vandavasi, J. K.; Chen, C. Y.; Wang, J. J. Facile, Selective, and Regiocontrolled Synthesis of Oxazolines and Oxazoles Mediated by ZnI2 and FeCl3. Org. Lett. 2012, 14, 4478–5581. (b) Hashmi, A. S. K.; Schuster, A. M.; Schmuck, M.; Rominger, F. Gold-Catalyzed Cyclization of Nonterminal Propargylic Amides to Substituted Alkylideneoxazolines and –Oxazines. Eur. J. Org. Chem. 2011, 2011, 4595–4602. (c) Hashmi, A. S. K.; Jaimes, M. C. B.; Schuster, A. M.; Rominger, F. From Propargylic Amides to Functionalized Oxazoles: domino Gold Catalysis/Oxidation by Dioxygen. J. Org. Chem. 2012, 77, 6394–6408.
   PubMed Web of Science ®Google Scholar
• (a) Kim, H.-S.; Lee, J.-Y.; Koh, Y. K.; Kwon, I.-C.; Choi, J.-H.; Suk, J. Y.; Lee, Y. R. Rhodium Catalyzed Reactions of Cyclic 2-Diazo-1,3-Dicarbonyl Compounds with Nitriles. Bull. Korean Chem. Soc. 1997, 18, 1222–1225. (b) Richard, C.; Frank, S.; Paul, H.; Björn, Å. Functionalized Oxazoles from Rhodiumi-Catalyzed Reaction of Dimethyl Diazomalonate with Nitriles. Tetrahedron Lett. 1986, 27, 5559–5562.
   Web of Science ®Google Scholar
• (a) Hossain, M. L.; Ye, F.; Zhang, Y.; Wang, J. Cu(I)-Catalyzed Reaction of Diazo Compounds with Terminal Alkynes: A Direct Synthesis of Trisubstituted Furans. Tetrahedron. 2014, 70, 6957–6962. (b) Pang, W.; Zhu, S.; Xin, Y.; Jiang, H.; Zhu, S. Rh2(OAc)4 Catalyzed Formation of Fluorine-Containing Polysubstituted Furans from Diazocompounds and Aromatic Alkynes. Tetrahedron. 2010, 66, 1261–1266. (c) Xia, L.; Lee, Y. R. Regioselective Synthesis of Highly Functionalized Furans through the RuII-Catalyzed [3 + 2] Cycloaddition of Diazodicarbonyl Compounds. Eur. J. Org. Chem. 2014, 2014, 3430–3442. (d) Kinder, F. R.; Padwa, A. Preparation of Oxygenated Heterocycles via the Cyclization Reaction of α-Diazo Substituted Alkynes. Tetrahedron Lett. 1990, 31, 6835–6838. (e) Padwa, A.; Kinder, F. R. Rhodium(II)-Catalyzed Cyclization of 2-Alkynyl 2-Diazo-3-Oxobutanoates as a Method for Synthesizing Substituted Furans. J. Org. Chem. 2010, 24, 28.
   Web of Science ®Google Scholar
• (a) Yu, X.; Xin, X.; Wan, B.; Li, X. Base-Catalyzed Cyclization of N-Sulfonyl Propargylamides to Sulfonylmethyl-Substituted Oxazoles via Sulfonyl Migration. J. Org. Chem. 2013, 78, 4895–4904. (b) Hu, Y.; Yi, R.; Wu, F.; Wan, B. Synthesis of Functionalized Oxazoles via Silver-Catalyzed Cyclization of Propargylamides and Allenylamides. J. Org. Chem. 2013, 78, 7714–7726. (c) Hu, Y. C.; Yi, R. X.; Wang, C. X.; Xin, X. Y.; Wu, F.; Wan, B. S. From Propargylamides to Oxazole Derivatives: NIS-Mediated Cyclization and Further Oxidation by Dioxygen. J. Org. Chem. 2014, 79, 3052–3059. (d) Gao, X.-H.; Qian, P.-C.; Zhang, X.-G.; Deng, C.-L. FeBr3-Catalyzed Tandem Reaction of N-Propargylamides with Disulfides or Diselenides for the Synthesis of Oxazole Derivatives. Synlett. 2016, 27, 1110–1115.
   PubMed Web of Science ®Google Scholar
• (a) Kuwano, R.; Kameyama, N.; Ikeda, R. Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles. J. Am. Chem. Soc. 2011, 133, 7312–7315. (b) Xu, Z. J.; Zhang, C.; Jiao, N. Synthesis of Oxazoles through Copper-Mediated Aerobic Oxidative Dehydrogenative Annulation and Oxygenation of Aldehydes and Amines. Angew. Chem. Int. Ed. 2012, 51, 11367–11370. (c) Saito, A.; Taniguchi, A.; Kambara, Y. Hanzawa.; Y, Metal-Free [2 + 2+1] Annulation of Alkynes, Nitriles, and Oxygen Atoms: Iodine(III)-Mediated Synthesis of Highly Substituted Oxazoles. Org. Lett. 2013, 15, 2672–2675. (d) Ritson, D. J.; Spiteri, C.; Moses, J. E. A Silver-Mediated One-Step Synthesis of Oxazoles. J. Org. Chem. 2011, 76, 3519–3522.
   PubMed Web of Science ®Google Scholar
• (a) Song, L.; Li, X.; Xing, C.; Li, D.; Zhu, S.; Deng, H.; Shao, M. Fluorine-Containing Furan Derivatives from the Michael Addition of Ethyl 4,4,4-Trifluoro-3-Oxobutanoate with β-Nitrostyrenes. Synlett. 2010, 5, 830–834. (b) Sousa, J. L. C.; Talhi, O.; Rocha, D. H. A.; Pinto, D. C. G. A.; Almeida, P.; F. A.; Bachari, K.; Kirsch, G.; Silva, A. M. S. One-Pot Synthesis of Novel Highly Functionalized Furan-Based Polyphenolics. Synlett. 2015, 26, 2724–2729.
   Google Scholar
• (a) Zhang, Y.; Wang, J.-B. Recent Development of Reactions with α-Diazocarbonyl Compounds as Nucleophiles. Chem. Commun. 2009, 2009, 5350–5361. (b) Zhang, Z.-H.; Wang, J.-B. Recent Studies on the Reactions of α-Diazocarbonyl Compounds. Tetrahedron. 2008, 64, 6577–6605. (c) Zhao, X.; Zhang, Y.; Wang, J.-B. Recent Developments in Copper-Catalyzed Reactions of Diazo Compounds. Chem. Commun. (Camb.) 2012, 48, 10162–10173.
   Google Scholar
• (a) Briones, J. F.; Davies, H. M. L. Gold(I)-Catalyzed Asymmetric Cyclopropenation of Internal Alkynes. J. Am. Chem. Soc. 2012, 134, 11916–11919. (b) Qin, C.-M.; Boyarskikh, V.; Hansen, J. H.; Hardcastle, K. I.; Musaev, D. G.; Davies, H. M. L. D2-Symmetric Dirhodium Catalyst Derived from a 1,2,2-Triarylcyclopropanecarboxylate Ligand: design, Synthesis and Application. J. Am. Chem. Soc. 2011, 133, 19198–19204. (c) Dudognon, Y.; Presset, M.; Rodriguez, J.; Coquerel, Y.; Bugaut, X.; Constantieux, T. Addition of Silylated Nucleophiles to α-Oxoketenes. Chem. Commun. (Camb.) 2016, 52, 3010–3013.
   PubMed Web of Science ®Google Scholar
• (a) Kischkewitz, M.; Daniliuc, C.-G.; Studer, A. 3. Alkylperoxy-3-Cyano-Oxindoles from 2-Cyano-2-Diazo-N-Phenyl-Acetamides via Cyclizing Carbene Insertion and Subsequent Radical Oxidation. Org. Lett. 2016, 18, 1206–1209. (b) Hyde, S.; Veliks, J.; Liégault, B.; Grassi, D.; Taillefer, M.; Gouverneur, V. V. Copper-Catalyzed Insertion into Heteroatom–Hydrogen Bonds with Trifluorodiazoalkanes. Angew. Chem. Int. Ed. 2016, 55, 3785–3789.
   PubMed Web of Science ®Google Scholar
• (a) So, S. S.; Mattson, A. E. Urea Activation of α-Nitrodiazoesters: An Organocatalytic Approach to N–H Insertion Reactions. J. Am. Chem. Soc. 2012, 134, 8798–8801. (b) Hansen, J. H.; Gergg, T. M.; Ovalles, S. R.; Autschbach, J.; Davies, H. M. L. On the Mechanism and Selectivity of the Combined C − H Activation/Cope Rearrangement. J. Am. Chem. Soc. 2011, 133, 5076–5085. (c) Huang, Z.; Wang, C.; Tokunaga, E.; Sumii, Y.; Shibata, N. Stereoselective Synthesis of β-Lactam-Triflones under Catalyst-Free Conditions. Org. Lett. 2015, 17, 5610–5613.
   PubMed Web of Science ®Google Scholar
• (a) Lian, Y.-J.; Miller, L. C.; Born, S.; Sarpong, R.; Davies, H. M. L. Catalyst-Controlled Formal [4 + 3] Cycloaddition Applied to the Total Synthesis of (+)-Barekoxide and (−)-Barekol. J. Am. Chem. Soc. 2010, 132, 12422–12425. (b) Chattopadhyay, B.; Gevorgyan, V. Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes. Org. Lett. 2011, 13, 3746–3749. (c) Xing, Y. P.; Sheng, G. R.; Wang, J.; Lu, P.; Wang, Y. G. Preparation of Triazoloindoles via Tandem Copper Catalysis and Their Utility as α-Imino Rhodium Carbene Precursors. Org. Lett. 2014, 16, 1244–1247. (d) Ren, A. N.; Lang, B.; Lin, J. L.; Lu, P.; Wang, Y. G. 4-Diazoisochroman-3-Imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives. J. Org. Chem. 2017, 82, 10953–10959.
   PubMed Web of Science ®Google Scholar
• Schwartz, B. D.; Denton, J. R.; Lian, Y.; Davies, H. M. L.; Williams, C. M. Asymmetric [4 + 3] Cycloadditions between Vinylcarbenoids and Dienes: application to the Total Synthesis of the Natural Product (−)-5-Epi-Vibsanin E. J. Am. Chem. Soc. 2009, 131, 8329–8332.
   PubMed Web of Science ®Google Scholar
• (a) Mondal, S.; Nechab, M.; Campolo, D.; Vanthuyne, N.; Bertrand, M. P. Copper Carbenoid, Reactant and Catalyst for One-Pot Diazo Ester Coupling Cascade Rearrangement of Enediynes: formation of Two Contiguous Tetrasubstituted Stereocenters. Adv. Synth. Catal. 2012, 354, 1987–2000. (b) Jadhav, A. M.; Pagar, V. V.; Liu, R.-S. Development of a Povarov Reaction/Carbene Generation Sequence for Alkenyldiazocarbonyl Compounds. Angew. Chem. Int. Ed. 2012, 51, 11809–11813. (c) Xu, X.-F.; Zavalij, P. Y.; Hu, W.-H.; Doyle, M. P. Vinylogous Reactivity of Enol Diazoacetates with Donor–Acceptor Substituted Hydrazones. synthesis of Substituted Pyrazole Derivatives. J. Org. Chem. 2013, 78, 1583–1588.
   Web of Science ®Google Scholar
• (a) Basso, A.; Banfi, L.; Garbarino, S.; Riva, R. Ketene Three-Component Reaction: A Metal-Free Multicomponent Approach to Stereodefined Captodative Olefins. Angew. Chem. Int. Ed. 2013, 52, 2096–2099. (b) Zhou, C.-Y.; Wang, J.-C.; Wei, J.-H.; Xu, Z.-J.; Guo, Z.; Low, K.-H.; Che, C.-M. Dirhodium Carboxylates Catalyzed Enantioselective Coupling Reactions of α-Diazophosphonates, Anilines, and Electron-Deficient Aldehydes. Angew. Chem. Int. Ed. 2012, 51, 11376–11380.
   PubMed Web of Science ®Google Scholar
• (a) Hu, M.-Y.; Ni, C.-F.; Hu, J.-B. Copper-Mediated Trifluoromethylation of α-Diazo Esters with TMSCF3: The Important Role of Water as a Promoter. J. Am. Chem. Soc. 2012, 134, 15257–15260. (b) Wu, Y.; Sun, P.; Zhang, K.; Yang, T.; Yao, H.; Lin, A. Rh(III)-Catalyzed Redox-Neutral Annulation of pPrimary Benzamides with Diazo Compounds: Approach to Isoquinolinones. J. Org. Chem. 2016, 81, 2166–2173. (c) Mishra, N. K.; Choi, M.; Jo, H.; Oh, Y.; Sharma, S.; Han, S. H.; Jeong, T.; Han, S.; Lee, S.-Y.; Kim, I. S. Direct C–H Alkylation and Indole Formation of Anilines with Diazo Compounds under Rhodium Catalysis. Chem. Commun. 2015, 51, 17229–17232. (d) Hu, F.; Xia, Y.; Ye, F.; Liu, Z.; Ma, C.; Zhang, Y.; Wang, J. Rhodium(III)-Catalyzed Ortho Alkenylation of N-Phenoxyacetamides with N-Tosylhydrazones or Diazoesters through C-H Activation. Angew. Chem. Int. Ed. Engl. 2014, 53, 1364–1367.
   PubMed Web of Science ®Google Scholar
• (a) Presset, M.; Coquerel, Y.; Rodriguez, J. Microwave-Assisted Wolff Rearrangement of Cyclic 2-Diazo-1,3-Diketones: An Eco-Compatible Route to α-Carbonylated Cycloalkanones. J. Org. Chem. 2009, 74, 415–441. (b) Presset, M.; Coquerel, Y.; Rodriguez, J. Microwave-Assisted Domino and Multicomponent Reactions with Cyclic Acylketenes: expeditious Syntheses of Oxazinones and Oxazindiones. Org. Lett. 2009, 11, 5706–5709. (c) Galvez, J.; Castillo, J.-C.; Quiroga, J.; Rajzmann, M.; Rodriguez, J.; Coquerel, Y. Divergent Chemo-, Regio-, and Diastereoselective Normal Electron-Demand Povarov-Type Reactions with α-Oxo-Ketene Dienophiles. Org. Lett. 2014, 16, 4126–4129.
   PubMed Web of Science ®Google Scholar
• (a) Castillo, J.-C.; Presset, M.; Abonia, R.; Coquerel, Y. Rodriguez, J., Microwave-Aassisted Domino Benzannulation of α-Oxo Ketenes: Preparation of 1,3-Dihydro-2H-1,5-Benzodiazepin-2-Ones. Eur. J. Org. Chem. 2012, 2012, 2338–2345. (b) Mohanan, K.; Presset, M.; Mailhol, D.; Coquerel, Y.; Rodriguez, J. Catalyst- and Halogen-free Regioselective Friedel–Crafts α-Ketoacylations. Chem.-Eur. J. 2012, 18, 9217–9220. (c) Boddaert, T.; Coquerel, Y.; Rodriguez, J. Combination of Rearrangement with Metallic and Organic Catalyses – a Step- and Atom-Economical Approach to α-Spiroactones and -Lactams. Eur. J. Org. Chem. 2011, 2011, 5061–5070. (d) Boddaert, T.; Coquerel, Y.; Rodriguez, J. Expeditious Divergent Synthetic Approach to Polycyclic Terpene-like Molecules. Chemistry. 2011, 17, 2048–2051.
   Google Scholar
• (a) Presset, M.; Coquerel, Y.; Rodriguez, J. Periselectivity Switch of Acylketenes in Cycloadditions with 1-Azadienes: Microwave-Assisted Diastereoselective Domino Three-Component Synthesis of α-Spiro-δ-Lactams. Org. Lett. 2010, 12, 4212–4215. (b) Presset, M.; Mohanan, K.; Hamann, M.; Coquerel, Y.; Rodriguez, J. 1,3-Dipolar Cycloaddition of Hydrazones with α-Oxo-Ketenes: A Three-Component Stereoselective Entry to Pyrazolidinones and an Original Class of Spirooxindoles. Org. Lett. 2011, 13, 4124–4127. (c) Castillo, J.-C.; Quiroga, J.; Rodriguez, J.; Coquerel, Y. Time-Efficient Synthesis of Pyrido[2,3-d]Pyrimidinones via α-Oxoketenes. Eur. J. Org. Chem. 2016, 2016, 1994–1999.
   PubMed Web of Science ®Google Scholar
• (a) Kim, H.-S.; Lee, J.-Y.; Koh, Y. K.; Kwon, I.-C.; Choi, J.-H.; Suk, J. Y.; Lee, Y. R. Rhodium Catalyzed Reactions of Cyclic 2-Diazo-1,3-Dicarbonyl Compounds with Nitriles. Bull. Korean Chem. Soc. 1997, 18, 1222–1225. (b) Xia, L.; Lee, Y. R. Regioselective Synthesis of Highly Functionalized Furans through the RuII-Catalyzed [3 + 2] Cycloaddition of Diazodicarbonyl Compounds. Eur. J. Org. Chem. 2014, 2014, 3430–3442. (c) Magar, K. B. S.; Lee, Y. R.; Kim, S. H. Efficient One-Pot Synthesis of Biologically Interesting Diverse Furo[2,3-b]Pyran-6-Ones by Rhodium(II)-Catalyzed Cascade Reactions of Diazo Compound with Ethynyl Compounds. Tetrahedron. 2013, 69, 9294–9302.
   Web of Science ®Google Scholar
• (a) Shi, J.; Zhou, J.; Yan, Y.; Jia, J.; Liu, X.; Song, H.; Xu, H. E.; Yi, W. One-Pot Cascade Synthesis of N-Methoxyisoquinolinediones via Rh(III)-Catalyzed Carbenoid Insertion C–H Activation/Cyclization. Chem. Commun. 2015, 51, 668–671. (b) Dudognon, Y.; Presset, M.; Rodriguez, J.; Coquerel, Y.; Bugaut, X.; Constantieux, T. Addition of Silylated Nucleophiles to α-Oxoketenes. Chem. Commun. 2016, 52, 3010–3013. (c) Sharma, S.; Han, S. H.; Han, S.; Ji, W.; Oh, J.; Lee, S.-Y.; Oh, J. S.; Jung, Y. H.; Kim, I. S. Rh(III)-Catalyzed Direct Coupling of Azobenzenes with α-Diazo Esters: facile Synthesis of Cinnolin-3(2H)-Ones. Org. Lett. 2015, 17, 2852–2855.
   PubMed Web of Science ®Google Scholar
• (a) Yang, C.; He, X.; Zhang, L.; Han, G.; Zuo, Y.; Shang, Y. Synthesis of Isocoumarins from Cyclic 2-Diazo-1,3-Diketones and Benzoic Acids via Rh(III)-Catalyzed C–H Activation and Esterification. J. Org. Chem. 2017, 82, 2081–2088. (b) He, X.; Zhou, Y.; Shang, Y.; Yang, C. Zuo, Y. Synthesis of 2-Arylimino-6,7-Dihydrobenzo[d][1,3]Oxathiol-4(5H)-Ones via Rh2(OAc)4-Catalyzed Reactions of Cyclic 2-Diazo-1,3-Diketones with Aryl Isothiocyanates. ACS Omega. 2016, 1, 1277–1283. (c) He, X.; Yu, Z.; Zuo, Y.; Yang, C.; Shang, Y. Direct Carboxamidation of Cyclic 2-Diazo-1,3-Diketones by Rh2(OAc)4-Catalyzed Isocyanide Insertion-Hydrolysis. Org. Biomol. Chem. 2017, 15, 7127–7130. (d) He, X.; Zhou, Y.; Shang, Y.; Yang, C.; Zuo, Y. Y. Rh(III)-Catalyzed C-H Activation/Intramolecular Cyclization: access to N-Acyl-2,3-Dihydro-1H-Carbazol-4(9H)-Ones from Cyclic 2-Diazo-1,3-Diketones and N-Arylamides. ACS Omega. 2016, 1, 1277–8516.
   PubMed Web of Science ®Google Scholar
• (a) Chupraov, S.; Kwok, S. W.; Fokin, V. V. Transannulation of 1-Sulfonyl-1,2,3-Triazoles with Heterocumulenes. J. Am. Chem. Soc. 2013, 135, 4652–4655. (b) Nikolaev, V. A.; Ivanov, A. V.; Rodina, L. L.; Mlostoń, G. Less Reactive Dipoles of Diazodicarbonyl Compounds in Reaction with Cycloaliphatic Thioketones – First Evidence for the 1,3-Oxathiole–Thiocarbonyl Ylide Interconversion. Beilst. J. Org. Chem. 2013, 9, 2751–2761. (c) Mlostoń, G.; Heimgartner, H. Synthesis of Five-Membered Sulfur-Heterocycles via 1,5-Dipolar Electrocyclization of Thiocarbonyl Ylides and Related Processes. Current Org. Chem. 2011, 15, 675. (d) Shao, Z.-H.; Zhang, H.-B. N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Cross-Coupling Reactions. Chem. Soc. Rev. 2012, 41, 560–572.
   PubMed Web of Science ®Google Scholar