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Synthesis 2017; 49(13): 2949-2957
DOI: 10.1055/s-0036-1588775
DOI: 10.1055/s-0036-1588775
paper
Convenient Phenacene Synthesis by Sequentially Performed Wittig Reaction and Mallory Photocyclization Using Continuous-Flow Techniques
Supported by: Japan Society for the Promotion of Science (JSPS) Grant-in-Aid for Scientific Research (KAKENHI JP26288032)Further Information
Publication History
Received: 18 February 2017
Accepted after revision: 13 March 2017
Publication Date:
24 April 2017 (online)
Abstract
Various phenacenes possessing chrysene, picene, and fulminene frameworks were prepared by using a continuous-flow synthetic protocol in which Wittig reaction affording diarylethenes and their Mallory photocyclization producing phenacene skeletons were sequentially performed. The Wittig reaction solution, containing the diarylethene obtained from an arylaldehyde and an arylmethyltriphenylphosphonium salt, was mixed with an iodine solution in the flow system and, subsequently, the solution was subjected to the photoreaction. Desired phenacenes were obtained with high to moderate chemical yield. For the present protocol, isolation of the intermediary diarylethene, which is the key precursor of the phenacene, is unnecessary. The approach provides a convenient method to supply a variety of phenacene samples, which are needed for initial systematic surveys in material science.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588775.
- Supporting Information
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References
- 1 Operamolla A. Farinola GM. Eur. J. Org. Chem. 2011; 423
- 2 Dong H. Fu X. Liu J. Wang Z. Hu W. Adv. Mater. 2013; 25: 6158
- 3 Zhou K. Dong H. Zhang H.-l. Hu W. Phys. Chem. Chem. Phys. 2014; 16: 22448
- 4 Anthony JE. Angew. Chem. Int. Ed. 2008; 47: 452
- 5 Anthony JE. Chem. Rev. 2006; 106: 5028
- 6 Yang X. Xu X. Zhou G. J. Mater. Chem. C 2015; 3: 913
- 7 Mitsuhashi R. Suzuki Y. Yamanari Y. Mitamura H. Kambe T. Ikeda N. Okamoto H. Fujiwara A. Yamaji M. Kawasaki N. Maniwa Y. Kubozono Y. Nature 2010; 464: 76
- 8 Kubozono Y. Mitamura H. Lee X. He X. Yamanari Y. Takahashi Y. Suzuki Y. Kaji Y. Eguchi R. Akaike K. Kambe T. Okamoto H. Fujiwara A. Kato T. Kosugi T. Aoki H. Phys. Chem. Chem. Phys. 2011; 13: 16476
- 9 Kubozono Y. Eguchi R. Goto H. Hamao S. Kambe T. Terao T. Nishiyama S. Zheng L. Miao X. Okamoto H. J. Phys.: Condens. Matter 2016; 28: 334001
- 10 Nakagawa T. Yuan Z. Zhang J. Yusenko KV. Drathen C. Liu Q.-Q. Margadonna S. Jin C. J. Phys.: Condens. Matter 2016; 28: 484001
- 11 Gundlach DJ. Lin YY. Jackson TN. Nelson SF. Schlom DG. IEEE Electron Device Lett. 1997; 18: 87
- 12 Okamoto H. Kawasaki N. Kaji Y. Kubozono Y. Fujiwara A. Yamaji M. J. Am. Chem. Soc. 2008; 130: 10470
- 13 Eguchi R. He X. Hamao S. Goto H. Okamoto H. Gohda S. Sato K. Kubozono Y. Phys. Chem. Chem. Phys. 2013; 15: 20611
- 14 He X. Hamao S. Eguchi R. Goto H. Yoshida Y. Saito G. Kubozono Y. J. Phys. Chem. C 2014; 118: 5284
- 15 Okamoto H. Eguchi R. Hamao S. Goto H. Gotoh K. Sakai Y. Izumi M. Takaguchi Y. Gohda S. Kubozono Y. Sci. Rep. 2014; 4: 5330
- 16 Shimo Y. Mikami T. Hamao S. Goto H. Okamoto H. Eguchi R. Gohda S. Hayashi Y. Kubozono Y. Sci. Rep. 2016; 6: 21008
- 17 Itoh T. Yamaji M. Okamoto H. Chem. Phys. Lett. 2013; 570: 26
- 18 Lang KF. Angew. Chem. 1951; 63: 345
- 19 Mallory FB. Mallory CW. Org. React. 1984; 30: 1
- 20 Jørgensen KB. Molecules 2010; 15: 4334
- 21 Knowles JP. Elliott LD. Booker-Milburn KI. Beilstein J. Org. Chem. 2012; 8: 2025
- 22 Mizuno K. Nishiyama Y. Ogaki T. Terao K. Ikeda H. Kakiuchi K. J. Photochem. Photobiol., C 2016; 29: 107
- 23 Lefebvre Q. Jentsch M. Rueping M. Beilstein J. Org. Chem. 2013; 9: 1883
- 24 Hernandez-Perez AC. Vlassova A. Collins SK. Org. Lett. 2012; 14: 2988
- 25 Okamoto H. Takane T. Gohda S. Kubozono Y. Sato K. Yamaji M. Satake K. Chem. Lett. 2014; 43: 994
- 26 Mallory FB. Butler KE. Evans AC. Mallory CW. Tetrahedron Lett. 1996; 37: 7173
- 27 Mallory FB. Butler KE. Evans AC. Brondyke EJ. Mallory CW. Yang C. Ellenstein A. J. Am. Chem. Soc. 1997; 119: 2119
- 28 Mallory FB. Butler KE. Bérubé A. Luzik ED. Jr. Mallory CW. Brondyke EJ. Hiremath R. Ngo P. Carroll PJ. Tetrahedron 2001; 57: 3715
- 29 Okamoto H. Yamaji M. Gohda S. Sato K. Sugino H. Satake K. Res. Chem. Intermed. 2013; 39: 147
- 30 Sydnes LK. Burkow IC. Hansen SH. Acta Chem. Scand., Ser. B 1985; 39: 829
- 31 Splitter JS. Calvin M. J. Org. Chem. 1955; 20: 1086
- 32 Okamoto H. Yamaji M. Gohda S. Kubozono Y. Komura N. Sato K. Sugino H. Satake K. Org. Lett. 2011; 13: 2758
- 33 Ho T.-I. Wu J.-Y. Wang S.-L. Angew. Chem. Int. Ed. 1999; 38: 2558
- 34 Lvov AG. Shirinian VZ. Zakharov AV. Krayushkin MM. Kachala VV. Zavarzin IV. J. Org. Chem. 2015; 80: 11491
- 35 McMillen DF. Golden DM. Ann. Rev. Phys. Chem. 1982; 33: 493
- 36 Benson SW. J. Chem. Educ. 1965; 42: 502
- 37 Paul S. Jana R. Ray JK. Synlett 2010; 1463
- 38 Ma Y.-G. Lei YD. Xiao H. Wania F. Wang W.-H. J. Chem. Eng. Data 2010; 55: 819
- 39 Archer WJ. Taylor R. Gore PH. Kamounah FS. J. Chem. Soc., Perkin Trans. 2 1980; 1828
- 40 Leznoff CC. Hayward RJ. Can. J. Chem. 1972; 50: 528
- 41 Gore PH. Kamonah FS. Synthesis 1978; 773
- 42 Phillips DD. J. Am. Chem. Soc. 1953; 75: 3223
- 43 Nasipuri D. J. Chem. Soc. 1958; 2618
- 44 Harvey RG. Pataki J. Cortez C. Raddo PD. Yang CX. J. Org. Chem. 1991; 56: 1210