Synlett 2013; 24(20): 2709-2714
DOI: 10.1055/s-0033-1338983
letter
© Georg Thieme Verlag Stuttgart · New York

A Combination of Copper(0) Powder and Selectfluor Enables Generation of Cationic Copper Species for Mild 1,2-Dicarbonylation of Alkynes

Wenxia Zhang
State Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, P. R. of China   Fax: +86(571)88320066   Email: ykuiliu@zjut.edu
,
Jian Zhang
State Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, P. R. of China   Fax: +86(571)88320066   Email: ykuiliu@zjut.edu
,
Yunkui Liu*
State Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, P. R. of China   Fax: +86(571)88320066   Email: ykuiliu@zjut.edu
,
Zhenyuan Xu
State Key Laboratory Breeding Base of Green Chemistry–Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, P. R. of China   Fax: +86(571)88320066   Email: ykuiliu@zjut.edu
› Author Affiliations
Further Information

Publication History

Received: 08 August 2013

Accepted after revision: 08 September 2013

Publication Date:
05 November 2013 (online)


Abstract

A combination of copper powder and Selectfluor permits the generation of cationic copper species that efficiently catalyze 1,2-dicarbonylation of alkynes under mild conditions with water and dioxygen as inexpensive and environmentally benign sources of oxygen.

Supporting Information

 
  • References and Notes

    • 1a Maurya R, Singh R, Deepak M, Handa SS, Yadav PP, Mishra PK. Phytochemistry 2004; 65: 915
    • 1b Yamamoto Y, Kimachi T, Kanaoka Y, Kato S, Bessho K, Matsumoto T, Kusakabe T, Sugiura Y. Tetrahedron Lett. 1996; 37: 7801
    • 1c Wadkins RM, Hyatt JL, Wei X, Yoon KJ. P, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM. J. Med. Chem. 2005; 48: 2906
    • 1d Harada T, Nakagawa Y, Wadkins RM, Potter PM, Wheelock CE. Bioorg. Med. Chem. 2009; 17: 149
    • 2a Sato N In Comprehensive Heterocyclic Chemistry II . Vol. 6. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 233
    • 2b Martorana A, Pace A, Buscemi S, Piccionello AP. Org. Lett. 2012; 14: 3240
    • 2c Deng X, Mani NS. Org. Lett. 2006; 8: 269
    • 2d Wolkenberg SE, Wisnoski DD, Leister H, Wang Y, Zhao Z, Lindsley CW. Org. Lett. 2004; 6: 1453
    • 2e Martínez V, Burgos C, Alvarez-Builla J, Fernández G, Domingo A, García-Nieto R, Gago F, Manzanares I, Cuevas C, Vaquero JJ. J. Med. Chem. 2004; 47: 1136
    • 2f Wärnmark K, Thomas JA, Heyke O, Lehn J.-M. Chem. Commun. 1996; 701
    • 2g Wright MW, Welker ME. J. Org. Chem. 1996; 61: 133
    • 2h Yamashita M, Okuyama K, Kawasaki I, Ohta S. Tetrahedron Lett. 1996; 37: 7755
    • 3a Tummatorn J, Khorphueng P, Petsom A, Muangsin N, Chaichit N, Roengsumran S. Tetrahedron 2007; 63: 11878
    • 3b Ren W, Liu J, Chen L, Wan X. Adv. Synth. Catal. 2010; 352: 1424
    • 3c Che C.-M, Yu W.-Y, Chan P.-M, Cheng W.-C, Peng S.-M, Lau K.-C, Li W.-K. J. Am. Chem. Soc. 2000; 122: 11380
    • 3d Al-Rashid ZF, Johnson WL, Hsung RP, Wei Y, Yao P.-Y, Liu R, Zhao K. J. Org. Chem. 2008; 73: 8780
    • 3e Gao A, Yang F, Li J, Wu Y. Tetrahedron 2012; 68: 4950
    • 3f Chandrasekhar S, Reddy NK, Kumar VP. Tetrahedron Lett. 2010; 51: 3623
    • 3g Muzart J. J. Mol. Catal. A: Chem. 2011; 338: 7
    • 3h Mori S, Takubo M, Yanase T, Maegawa T, Monguchi Y, Sajiki H. Adv. Synth. Catal. 2010; 352: 1630
    • 3i Sawama Y, Takubo M, Mori S, Monguchi Y, Sajiki H. Eur. J. Org. Chem. 2011; 3361
    • 3j Ren W, Xia Y, Ji S.-J, Zhang Y, Wan X, Zhao J. Org. Lett. 2009; 11: 1841
    • 3k Mousset C, Provot O, Hamze A, Nignon J, Brioni J.-D, Alami M. Tetrahedron 2008; 64: 4287
    • 3l Xu C.-F, Xu M, Jia Y.-X, Li C.-Y. Org. Lett. 2011; 13: 1556
    • 3m Liu Y, Chen X, Zhang J, Xu Z. Synlett 2013; 24: 1371
    • 3n Giraud A, Provot O, Peyrat J.-F, Alami M, Brion J.-D. Tetrahedron 2006; 62: 7667
    • 3o Zhang C, Jiao N. J. Am. Chem. Soc. 2010; 132: 28
    • 3p Xu Y, Wan X. Tetrahedron Lett. 2013; 54: 642

      For syntheses of 1,2-dicarbonyl compounds by methods other than oxidations of alkynes involving transition metals, see for example:
    • 4a Khurana JM, Kandpal BM. Tetrahedron Lett. 2003; 44: 4909
    • 4b Tingoli M, Mazzella M, Panunzi B, Tuzi A. Eur. J. Org. Chem. 2011; 399
    • 4c Bhattacharya T, Sarma TK, Samanta S. Catal. Sci. Technol. 2012; 2: 2216
    • 4d Chang C.-L, Kumar MP, Liu R.-S. J. Org. Chem. 2004; 69: 2793
    • 4e Kashiwabara T, Tanaka M. J. Org. Chem. 2009; 74: 3958
    • 4f Chen S, Liu Z, Shi E, Chen L, Wei W, Li H, Cheng Y, Wan X. Org. Lett. 2011; 13: 2274
    • 4g Liu X, Chen W. Organometallics 2012; 31: 6614
    • 4h Du F.-T, Ji J.-X. Chem. Sci. 2012; 3: 460
    • 4i Wan Z, Jones CD, Mitchell D, Pu JY, Zhang TY. J. Org. Chem. 2006; 71: 826
    • 4j Zhang C, Zong X, Zhang L, Jiao N. Org. Lett. 2012; 14: 3280
    • 4k Zhao X.-F, Zhang C. Synthesis 2007; 551
    • 4l Qi C, Jiang H, Chen Z, Chen H. Synthesis 2011; 387
    • 4m Niu M, Fu H, Jiang Y, Zhao Y. Synthesis 2008; 2879
    • 4n Hayashi M, Shibuya M, Iwabuchi Y. Synlett 2012; 23: 1025
    • 4o Santoro S, Battistelli B, Gjoka B, Si C.-WS, Testaferri L, Tiecco M, Santi C. Synlett 2010; 1402
    • 4p Su Y, Zhang L, Jiao N. Org. Lett. 2011; 13: 2168
    • 4q Fa L, Chen W, Qian C. Tetrahedron Lett. 2013; 54: 231
    • 5a Doucet H, Hierso J.-C. Angew. Chem. Int. Ed. 2007; 46: 834
    • 5b Chinchilla R, Najera C. Chem. Rev. 2007; 107: 874
    • 6a Gligorich KM, Sigman MS. Chem. Commun. 2009; 3845
    • 6b Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
    • 7a Rach SF, Kühn FE. Chem. Rev. 2009; 109: 2061
    • 7b Krossing I, Raabe I. Angew. Chem. Int. Ed. 2004; 43: 2066
    • 8a Arcadi A. Chem. Rev. 2008; 108: 3266
    • 8b Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
    • 8c He Z, Liu T, Tao H, Wang C.-J. Org. Lett. 2012; 14: 6230
    • 8d Hernandez-Perez AC, Vlassova A, Collins SK. Org. Lett. 2012; 14: 2988
    • 8e Lebœuf D, Theiste E, Gandon V, Daifuku SL, Neidig ML, Frontier AJ. Chem. Eur. J. 2013; 19: 4842
    • 8f Zhu R, Buchwald SL. J. Am. Chem. Soc. 2012; 134: 12462
    • 8g Kozhushkov SI, Ackermann L. Chem. Sci. 2013; 4: 886
    • 8h Brasse M, Cámpora J, Ellman JA, Bergman RG. J. Am. Chem. Soc. 2013; 135: 6427
    • 8i Muralirajan K, Cheng C.-H. Chem. Eur. J. 2013; 19: 6198
  • 9 Buschmann WE, Miller JS. Inorg. Synth. 2002; 33: 83
  • 10 Teles JH, Brode S, Chabanas M. Angew. Chem. Int. Ed. 1998; 37: 1415
  • 11 Lavallo V, Frey GD, Kousar S, Donnadieu B, Bertrand G. Proc. Natl. Acad. Sci. U.S.A. 2007; 104: 13569
    • 12a Gaillard S, Bosson J, Ramón RS, Nun P, Slawin AM. Z, Nolan SP. Chem. Eur. J. 2010; 16: 13729
    • 12b Ramón RS, Gaillard S, Poater A, Cavallo L, Slawin AM. Z, Nolan SP. Chem. Eur. J. 2011; 17: 1238
    • 13a Wang W, Jasinski J, Hammond GB, Xu B. Angew. Chem. Int. Ed. 2010; 49: 7247
    • 13b Xu B, Wang W, Hammond GB. J. Fluorine Chem. 2011; 132: 804
  • 14 Crystallographic data for compound 6 have been deposited with the accession number CCDC 938347, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
  • 15 Schröder D, Holthausen MC, Schwarz H. J. Phys. Chem. B 2004; 108: 14407
  • 16 Fier PS, Luo J, Hartwig JF. J. Am. Chem. Soc. 2013; 135: 2552
  • 17 Giester G, Libowitzky E. Z. Kristallogr. 2003; 218: 351

    • For selected examples of redox reactions of transition-metal complexes with Selectfluor, see:
    • 18a Jin Z, Xu B, Hammond GB. Tetrahedron Lett. 2011; 52: 1956
    • 18b Brenzorich WE. Jr, Benitez D, Lackner AD, Shunatona HP, Tkatchouk E, Goddard III WA, Toste FD. Angew. Chem. Int. Ed. 2010; 49: 5519
    • 18c Li Z, Song L, Li C. J. Am. Chem. Soc. 2013; 135: 4640
  • 19 Wang Z.-Q, Zhang W.-W, Gong L.-B, Tang R.-Y, Yang X.-H, Liu Y, Li J.-H. Angew. Chem. Int. Ed. 2011; 50: 8968 ; and references cited therein
    • 20a Tsai W, Liu Y.-H, Peng SM, Liu S.-T. J. Organomet. Chem. 2005; 690: 415
    • 20b Liu Y, Zhu J, Qian J, Xu Z. J. Org. Chem. 2012; 77: 5411
    • 20c Lü B, Fu C, Ma S. Org. Biomol. Chem. 2010; 8: 274 ; and references cited therein