Synlett 2012; 23(7): 1074-1078
DOI: 10.1055/s-0031-1290526
letter
© Georg Thieme Verlag Stuttgart · New York

Unexpected Base-Promoted Synthesis of Tetrasubstituted Furans via Palla­dium-Catalyzed Oxidation and Cyclization of Carbon–Carbon Triple Bond with Molecular Oxygen

Lianyue Wang
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, P. R. of China
,
Jun Li*
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, P. R. of China
c   Dalian National Laboratory for Clean Energy, DNL, 457 Zhongshan Road, Dalian, Liaoning 116023, P. R. of China, Fax: +86(411)84379248   Email: junli@dicp.ac.cn   Email: sgao@dicp.ac.cn
,
Ying Lv
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, P. R. of China
c   Dalian National Laboratory for Clean Energy, DNL, 457 Zhongshan Road, Dalian, Liaoning 116023, P. R. of China, Fax: +86(411)84379248   Email: junli@dicp.ac.cn   Email: sgao@dicp.ac.cn
,
Gongda Zhao
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, P. R. of China
c   Dalian National Laboratory for Clean Energy, DNL, 457 Zhongshan Road, Dalian, Liaoning 116023, P. R. of China, Fax: +86(411)84379248   Email: junli@dicp.ac.cn   Email: sgao@dicp.ac.cn
,
Shuang Gao*
a   Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, P. R. of China
c   Dalian National Laboratory for Clean Energy, DNL, 457 Zhongshan Road, Dalian, Liaoning 116023, P. R. of China, Fax: +86(411)84379248   Email: junli@dicp.ac.cn   Email: sgao@dicp.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 05 January 2012

Accepted after revision: 14 February 2012

Publication Date:
29 March 2012 (online)


Abstract

A new approach to the synthesis of tetrasubstituted furans using aromatic alkynes catalyzed by PdCl2 in DMA (N,N-dimethylacetamide)–H2O with dioxygen as the sole oxidant is described, in which the oxygen atom of the furan was from water. The preliminary mechanistic understanding of this transformation was investigated.

Supporting Information

 
  • References and Notes

    • 1a Lipshutz BH. Chem. Rev. 1986; 86: 795
    • 1b Lee H.-K, Chan K.-F, Hui C.-W, Yim H.-K, Wu X.-W, Wong HN. C. Pure Appl. Chem. 2005; 77: 139
    • 1c Brown TH, Armitage MA, Blakemore RC, Blurton P, Durant GJ, Ganellin CR, Ife RJ, Parsons ME, Rawlings DA, Slingsby BP. Eur. J. Med. Chem. 1990; 217
    • 1d Keay BA, Dibble PW In Comprehensive Heterocyclic Chemistry II . Vol. 4. Katritzky AR, Rees CW, Scriven EF. V. Elsevier; Oxford: 1997: 395
    • 1e Wong HN. C, Yu P, Yick C.-Y. Pure Appl. Chem. 1999; 71: 1041
    • 1f Hou XL, Yang Z, Wong HN. C In Progress in Heterocyclic Chemistry . Vol. 15. Gribble GW, Gilchrist TL. Pergamon; Oxford: 2003: 167
    • 1g Donnelly MX, Meegan MJ In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 657
    • 1h Mortensen DJ, Rodriguez AL, Carlson KE, Sun J, Katzenellenbogen BS, Katzenellenbogen JA. J. Med. Chem. 2001; 44: 3838
    • 1i Flynn BL, Hamel E, Jung MK. J. Med. Chem. 2002; 45: 2670
    • For recent reviews, see:

    • 2a Cacchi S. J. Organomet. Chem. 1999; 576: 42
    • 2b Keay BA. Chem. Soc. Rev. 1999; 28: 209
    • 2c Hou XL, Cheung HY, Hon TY, Kwan PL, Lo TH, Tong SY, Wong HN. C. Tetrahedron 1998; 54: 1955
    • 2d Onitsuka S, Nishino H, Kurosawa K. Tetrahedron Lett. 2000; 41: 3149
    • 2e Dudnik AS, Sromek AW, Rubina M, Kim JT, Kel’in AV, Gevorgyan V. J. Am. Chem. Soc. 2008; 130: 1440
    • 2f Schwier T, Sromek AW, Yap DM. L, Chernyak D, Gevorgyan V. J. Am. Chem. Soc. 2007; 129: 9868
    • 2g Peng LL, Zhang X, Ma M, Wang JB. Angew. Chem. Int. Ed. 2007; 46: 1905
    • 2h Sromek AW, Rubina M, Gevorgyan V. J. Am. Chem. Soc. 2005; 127: 10500
    • 2i Xia YZ, Dudnik AS, Gevorgyan V, Li YH. J. Am. Chem. Soc. 2008; 130: 6940
    • 2j Feng X, Tan Z, Chen D, Shen Y, Guo C, Xiang J, Zhu C. Tetrahedron Lett. 2008; 49: 4110
    • 2k Cao H, Jiang H, Mai R, Zhu S, Qia C. Adv. Synth. Catal. 2010; 352: 143
    • For recent reviews, see:

    • 3a Nakano M, Tsurugi H, Satoh T, Miura M. Org. Lett. 2008; 10: 1851
    • 3b Kirsch SF. Org. Biomol. Chem. 2006; 4: 2076
    • 3c Kawai H, Oi S, Inoue Y. Heterocycles 2006; 67: 101
    • 3d Brown RC. D. Angew. Chem. Int. Ed. 2005; 44: 850
    • 3e Jeevanandam A, Ghule A, Ling Y.-C. Curr. Org. Chem. 2002; 6: 841
    • 3f Friedrichsen W. Furans and Benzo Derivatives: Synthesis, In Comprehensive Heterocyclic Chemistry II . Vol. 2. Katritzky AR, Rees CW, Scriven EF. V. Pergamon Press; Oxford: 1996: 351
    • 3g Hou XL, Cheung HY, Hon TY, Kwan PL, Lo TH, Tong SY, Wong HN. C. Tetrahedron 1998; 54: 1955
    • 3h Krasnoslobodskaya LD, Goldfarb YL. Russ. Chem. Rev. 1969; 38: 389
    • 3i Li Y, Yu Z. J. Org. Chem. 2009; 74: 8904
    • 3j Xiao Y, Zhang JL. Chem. Commun. 2010; 752
    • 3k Wang T, Zhang J. Dalton Trans. 2010; 39: 4270
    • 3l Dudnik AS, Gevorgyan V. Angew. Chem. Int. Ed. 2007; 46: 5195
    • For selected reviews, see:

    • 4a Hashmi AS. K, Schwarz L, Choi J.-H, Frost TM. Angew. Chem. Int. Ed. 2000; 39: 2285
    • 4b Fukuda Y, Shiragami H, Utimoto K, Nozaki H. J. Org. Chem. 1991; 56: 5815
    • 4c Sniady A, Wheeler KA, Dembinski R. Org. Lett. 2005; 7: 1769
    • For selected reviews, see:

    • 5a Gabriele B, Salerno G, Lauria E. J. Org. Chem. 1999; 64: 7687
    • 5b Seiller B, Bruneau C, Dixneuf PH. Tetrahedron 1995; 51: 13089
    • 5c Liu Y, Song F, Song Z, Liu M, Yan B. Org. Lett. 2005; 7: 5409
  • 6 Hashmi AS. K, Sinha P. Adv. Synth. Catal. 2004; 346: 432
  • 8 Typical Procedure for Substrate 1a: The reaction was carried out in a 150-mL Teflon-lined 316-L stainless steel autoclave and a magnetic stirrer. A mixture of PdCl2 (5 mol%, 0.025 mmol, 4.4 mg), NaOAc (5 mol%, 0.025 mmol, 2.1 mg), 1a (0.5 mmol, 89 mg), H2O (0.1 mL) and DMA (2 mL) was placed in the 150-mL Teflon-lined 316-L stainless steel autoclave. Then, 0.1 MPa of O2 was introduced. The mixture was stirred for 6 h at 80 °C. After the reaction, the reactor was quickly cooled to r.t. The excess of O2 was depressurized slowly. The products were extracted using a Et2O–H2O mixture (1:1; 3 × 20 mL). The Et2O layers containing the products were dried over Na2SO4, filtrated and concentrated under reduced pressure. The resultant crude mixture was purified by column chromatography (silica gel) with a mixture of EtOAc–hexane (1:20) as eluent to afford 2a (70 mg, yield 76%). The product was characterized by NMR and confirmed by comparison with the reported authentic NMR data
    • 9a Mitsudome T, Umetani T, Nosaka N, Mori K, Mizugaki T, Ebitani K, Kaneda K. Angew. Chem. Int. Ed. 2006; 45: 48
    • 9b Mitsudome T, Mizumoto K, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2010; 49: 1238
    • 9c Wang LY, Li J, Lv Y, Zhang HY, Gao S. J. Organomet. Chem. 2011; 696: 3257