Download PDF
Synlett 2010(7): 1071-1074  
DOI: 10.1055/s-0029-1219778
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I)-Catalyzed Synthesis of Polysubstituted Furans from Alkynoates and 1,3-Dicarbonyl Compounds in the Presence of Oxygen

Rulong Yan, Jing Huang, Jia Luo, Ping Wen, Guosheng Huang*, Yongmin Liang*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: hgs@lzu.edu.cn; e-Mail: liangym@lzu.edu.cn;
Further Information

Publication History

Received 15 January 2010
Publication Date:
17 March 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A novel and straightforward synthesis of polysubstituted furans was achieved easily from the oxidative cyclization of 1,3-dicarbonyl compound and alkynoate catalyzed by CuI in the presence of O2.

Key words

polysubstituted furans - oxidant - copper catalysis - oxygen.

    References and Notes

  • For selected reviews, see:
  • 1a Lipshutz BH. Chem. Rev.  1986,  86:  795 
    Google Scholar
  • 1b Dean FM. In Advances in Heterocyclic Chemistry   Vol. 31:  Katritzky AR. Academic Press; New York: 1983.  p.237 
    Google Scholar
  • 1c Jeevanandam A. Ghule A. Ling YC. Curr. Org. Chem.  2002,  6:  841 
    Google Scholar
  • 1d Brown RCD. Angew. Chem. Int. Ed.  2005,  44:  850 
    Google Scholar
  • 1e Kirsh SF. Org. Biomol. Chem.  2006,  4:  2076 
    Google Scholar
  • 1f Frère P. Skabara P. Chem. Soc. Rev.  2005,  34:  69 
    Google Scholar
  • 2a Wong HNC. Yu P. Yick CY. Pure Appl. Chem.  1999,  71:  1041 
    Google Scholar
  • 2b Lee K. Chan KF. Hui CW. Yim HK. Wu XW. Wong HNC. Pure Appl. Chem.  2005,  77:  139 
    Google Scholar
  • 2c Kao CL. Chern JW. J. Org. Chem.  2002,  67:  6772 
    Google Scholar
  • 2d Yang Z. Liu HB. Lee CM. Chang HM. Wong HNC. J. Org. Chem.  1992,  57:  7248 
    Google Scholar
  • 2e Flynn BL. Hamel E. Jung MK. J. Med. Chem.  2002,  45:  2670 
    Google Scholar
  • 2f Kerr DJ. Hamel E. Jung MK. Flynn BL. Bioorg. Med. Chem.  2007,  15:  3290 
    Google Scholar
  • 2g Flynn BL. Pinard P. Hamel E. Org. Lett.  2001,  3:  651 
    Google Scholar
  • 2h Wong HNC. Yang Y. Tetrahedron  1994,  50:  9583 
    Google Scholar
  • 2i Gabriele B. Salerno G. Lauria E. J. Org. Chem.  1999,  64:  7687 
    Google Scholar
  • 3 Minetto G. Raveglia LF. Sega A. Taddei M. Eur. J. Org. Chem.  2005,  24:  5277 ; and references cited therein
    CrossrefGoogle Scholar
  • 4a Hou XL. Cheung HY. Hon TY. Kwan PL. Lo TH. Tong SY. Wong HNC. Tetrahedron  1998,  54:  1955 
    Google Scholar
  • 4b Krasnoslobodskaya LD. Gol’dfarb YL. Russ. Chem. Rev.  1969,  38:  389 
    Google Scholar
  • 5a Hashmi ASK. Schwarz L. Choi JH. Frost TM. Angew. Chem. Int. Ed.  2000,  39:  2385 
    Google Scholar
  • 5b Zhou CY. Chan PWH. Che CM. Org. Lett.  2006,  8:  325 
    Google Scholar
  • 5c Liu WB. Jiang HF. Zhou P. Zhu SF. Synlett  2009,  3295 
    Google Scholar
  • 5d Zhang M. Jiang HF. Wang AZ. Synlett  2007,  3241 
    Google Scholar
  • 5e Cao H. Jiang HF. Yao WJ. Org. Lett.  2009,  11:  1931 
    Google Scholar
  • 5f Yao T. Zhang X. Larock RC. J. Org. Chem.  2005,  70:  7679 
    Google Scholar
  • 5g Patil NT. Wu H. Yamamoto Y. J. Org. Chem.  2005,  70:  4531 
    Google Scholar
  • 5h Liu Y. Zhou S. Org. Lett.  2005,  7:  4609 
    Google Scholar
  • 5i Sromek AW. Rubina M. Gevorgyan V. J. Am. Chem. Soc.  2005,  127:  10500 
    Google Scholar
  • 5j Ma MS. Zhang J. Lu L. Chem. Eur. J.  2003,  9:  2447 
    Google Scholar
  • 5k Suhre MH. Reif M. Kirsch SF. Org. Lett.  2005,  7:  3925 
    Google Scholar
  • 5l Cadierno V. Crochet P. Curr. Org. Synth.  2008,  5:  343 
    Google Scholar
  • 6 Li C.-J. Acc. Chem. Res.  2009,  42:  2335 ; and references therein
    Google Scholar
  • For some reviews, see:
  • 7a Punniyamurthy T. Velusamy S. Iqbal J. Chem. Rev.  2005,  105:  2329 
    Google Scholar
  • 7b Stahl SS. Angew. Chem. Int. Ed.  2004,  43:  400 
    Google Scholar
  • 8a Fan M. Guo L. Liu X. Liu W. Liang YM. Synthesis  2005,  391 
    Google Scholar
  • 8b Fan M. Yan Z. Liu W. Liang YM. J. Org. Chem.  2005,  70:  8204 
    Google Scholar
  • 8c Duan X. Liu X. Guo L. Liao M. Liu W. Liang YM. J. Org. Chem.  2005,  70:  6980 
    Google Scholar
  • 8d Shu X.-Z. Liu X.-Y. Xiao H.-Q. Ji K.-G. Guo L.-N. Qi C.-Z. Liang Y.-M. Adv. Synth. Catal.  2008,  50:  243 
    Google Scholar
  • 8e Shu X.-Z. Liu X.-Y. Ji K.-G. Xiao H.-Q. Liang Y.-M. Chem. Eur. J.  2008,  14:  5282 
    Google Scholar
  • 8f Ji K.-G. Shen Y.-W. Shu X.-Z. Xiao H.-Q. Bian Y.-J. Liang Y.-M. Adv. Synth. Catal.  2008,  350:  1275 
    Google Scholar
  • 8g Zhao L.-B. Guan Z.-H. Han Y. Xie Y.-X. He S. Liang Y.-M. J. Org. Chem.  2007,  72:  10276 
    Google Scholar
  • 9 Christoffer J. Eur. J. Org. Chem.  1998,  7:  1259 
    Google Scholar
  • 10a Sawada D. Kanai M. Shibasaki M. J. Am. Chem. Soc.  2000,  122:  10521 
    Google Scholar
  • 10b Gurjar MK. Maheshwar K. J. Org. Chem.  2001,  66:  7552 
    Google Scholar
  • 10c Ying BP. Trogden BG. Kohlman DT. Liang SX. Xu YC. Org. Lett.  2004,  6:  1523 
    Google Scholar
11

General Procedure for the Preparation of Dimethyl But-2-yndioate and 1,3-Diphenyl-1,3-propanedione (3aa)
An oven-dried Schlenk tube was charged with CuI (9.5 mg, 0.05 mmol), 1a (0.50 mmol), and 2a (0.50 mmol). The Schlenk tube was sealed and then evacuated and backfilled with oxygen (3 cycles). Then DMF (2 mL) was added to the reaction system. The reaction was stirred at 110 ˚C under O2 (1 atm) for 4 h. After cooling to r.t., the solvent diluted with Et2O (10 mL) and washed with brine (5 mL) and dried over anhyd Na2SO4. After the solvent was evaporated in vacuo, the residues were purified by column chromatography, eluting with PE-EtOAc (10:1) to afford pure 3aa.
Dimethyl 4-Benzoyl-5-phenylfuran-2, 3-dicarboxylate (3aa) Yellow viscous oil. ¹H NMR (400 MHz CDCl3): δ = 3.61 (s, 3 H), 3.96 (s, 3 H), 7.29-7.39 (m, 5 H), 7.50-7.54 (m, 1 H), 7.61-7.63 (m, 2 H), 7.79-7.81 (m, 2 H). ¹³C NMR (100 MHz, CDCl3): δ = 52.4, 52.5, 121.5, 126.2, 127.4, 127.6, 128.5, 128.6, 129.3, 130.2, 133.6, 136.7, 141.1, 155.3, 157.7, 161.9, 190.0. IR (neat): 694, 772, 899, 1080, 1167, 1235, 1443, 1666, 1730, 2953, 3004, 3062 cm-¹. HRMS (EI): m/z calcd for C21H16O6 [M + H]+: 365.1020; found: 365.1029.
The ¹H NMR, ¹³C NMR, IR, and HRMS data of 3aa-bb can be found in the Supporting Information.