European Journal of Organic Chemistry
10.1002/ejoc.201601406
COMMUNICATION
the same temperature for 20 min, the reaction was quenched with
phosphate buffer (pH 7). Organic materials were extracted with CH2Cl2
three times, and the combined extracts were washed with brine and dried
over Na2SO4. After removal of the solvents under reduced pressure, the
residue was purified by silica gel column chromatography
(hexane/CH2Cl2 = 5:1) to give 2-bromophenanthrene (2e, 1.83 g, 99%)
as a white solid.
[9]
For self-aldol oligomerization of arylacetaldehydes, see: M. Tena-
Solsona, J. Nanda, S. Díaz-Oltra, A. Chotera, G. Ashkenasy, B.
Escuder, Chem. Eur. J. 2016, 22, 6687-6694.
[10] a) J. Ichikawa, S. Miyazaki, M. Fujiwara, T. Minami, J. Org. Chem. 1995,
60, 2320-2321; b) J. Ichikawa, Pure Appl. Chem. 2000, 72, 1685-1689;
c) J. Ichikawa, H. Jyono, T. Kudo, M. Fujiwara, M. Yokota, Synthesis
2005, 39-46; d) J. Ichikawa, M. Kaneko, M. Yokota, M. Itonaga, T.
Yokoyama, Org. Lett. 2006, 8, 3167-3170; e) M. Yokota, D. Fujita, J.
Ichikawa, Org. Lett. 2007, 9, 4639-4642; f) J. Ichikawa, M. Yokota, T.
Kudo, S. Umezaki, Angew. Chem. 2008, 120, 4948-4951; Angew.
Chem. Int. Ed. 2008, 47, 4870-4873; g) H. Isobe, S. Hitosugi, T.
Matsuno, T. Iwamoto, J. Ichikawa, Org. Lett. 2009, 11, 4026-4028; h) H.
Tanabe, J. Ichikawa, Chem. Lett. 2010, 39, 248-249; i) K. Fuchibe, H.
Jyono, M. Fujiwara, T. Kudo, M. Yokota, J. Ichikawa, Chem. Eur. J.
2011, 17, 12175-12185; j) K. Fuchibe, T. Morikawa, K. Shigeno, T.
Fujita, J. Ichikawa, Org. Lett. 2015, 17, 1126-1129; k) K. Fuchibe, T.
Morikawa, R. Ueda, T. Okauchi, J. Ichikawa, J. Fluorine Chem. 2015,
179, 106-115; l) N. Suzuki, T. Fujita, J. Ichikawa, Org. Lett. 2015, 17,
4984-4987; m) T. Fujita, Y. Watabe, S. Yamashita, H. Tanabe, T.
Nojima, J. Ichikawa, Chem. Lett. 2016, 45, 964-966.
Acknowledgements
This work was financially supported by JSPS KAKENHI Grant
Number JP16H04105 (J.I.). We acknowledge the generous gift
of (CF3)2CHOH (HFIP) from Central Glass Co., Ltd.
Keywords: fluoroalcohols • Brønsted acids • catalysts •
cyclization • aromatic compounds
[11] For reviews, see: a) J.-P. Bégué, D. Bonnet-Delpon, B. Crousse,
Synlett 2004, 18-29; b) I. A. Shuklov, N. V. Dubrovina, A. Börner,
Synthesis 2007, 2925-2943; c) T. Dohi, N. Yamaoka, Y. Kita,
Tetrahedron 2010, 66, 5775-5785; d) S. Khaksar, J. Fluorine Chem.
2015, 172, 51-61.
[1]
[2]
R. G. Harvey in Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New
York, 1997.
For reviews, see: a) J. E. Anthony, Chem. Rev. 2006, 106, 5028-5048;
b) J. E. Anthony, Angew. Chem. 2008, 120, 460-492; Angew. Chem. Int.
Ed. 2008, 47, 452-483; c) Y. Yamashita, Sci. Technol. Adv. Mater. 2009,
10, 024313; d) Y. Kubozono, X. He, S. Hamao, K. Teranishi, H. Goto, R.
Eguchi, T. Kambe, S. Gohda, Y. Nishihara, Eur. J. Inorg. Chem. 2014,
3806-3819; e) M. Rickhaus, M. Mayor, M. Juríček, Chem. Soc. Rev.
2016, 45, 1542-1556.
[12] For selected papers on carbocationic processes in HFIP reported by
other groups, see: a) N. Nishiwaki, R. Kamimura, K. Shono, T.
Kawakami, K. Nakayama, K. Nishino, T. Nakayama, K. Takahashi, A.
Nakamura, T. Hosokawa, Tetrahedron Lett. 2010, 51, 3590-3592; b) P.
A. Champagne, Y. Benhassine, J. Desroches, J.-F. Paquin, Angew.
Chem. 2014, 126, 14055-14059; Angew. Chem. Int. Ed. 2014, 53,
13835-13839; c) E. Gaster, Y. Vainer, A. Regev, S. Narute, K.
Sudheendran, A. Werbeloff, H. Shalit, D. Pappo, Angew. Chem. 2015,
127, 4272-4276; Angew. Chem. Int. Ed. 2015, 54, 4198-4202; d) C. L.
Ricardo, X. Mo, J. A. McCubbin, D. G. Hall, Chem. Eur. J. 2015, 21,
4218-4223; e) H. F. Motiwala, R. H. Vekariya, J. Aubé, Org. Lett. 2015,
17, 5484-5487.
[3]
For synthesis of phenacenes via photochemical oxidative cyclization
(Mallory reaction), see: a) F. B. Mallory, C. W. Mallory, Org. React.
1984, 30, 1-456, and references cited therein; b) F. B. Mallory, K. E.
Butler, A. C. Evans, E. J. Brondyke, C. W. Mallory, C. Yang, A.
Ellenstein, J. Am. Chem. Soc. 1997, 119, 2119-2124; c) F. B. Mallory, K.
E. Butler, A. Bérubé, E. D. Luzik, Jr., C. W. Mallory, E. J. Brondyke, R.
Hiremath, P. Ngo, P. J. Carroll, Tetrahedron 2001, 57, 3715-3724; d) H.
Okamoto, M. Yamaji, S. Gohda, Y. Kubozono, N. Komura, K. Sato, H.
Sugino, K. Satake, Org. Lett. 2011, 13, 2758-2761; e) M. Chen, C.
Yang, Y. Wang, D. Li, W. Xia, Org. Lett. 2016, 18, 2280-2283.
For synthesis of phenacenes via the McMurry coupling, see: a) A.-E.
Gies, M. Pfeffer, J. Org. Chem. 1999, 64, 3650-3654; b) S. Some, B.
Dutta, J. K. Ray, Tetrahedron Lett. 2006, 47, 1221-1224.
[13] X.-X. Zhang, S. J. Lippard, J. Org. Chem. 2000, 65, 5298-5305.
[14] Cycloaromatization of
a CF3-bearing arene substrate proceeded
unprecedentedly. See also Table 2, Entry 4 in ref. 19b.
[15] Cycloaromatization for the naphthyl-bearing substrates proceeded in
accordance with the regioselsectivity observed in normal electrophilic
aromatic substitution reactions.
[4]
[5]
[6]
For synthesis of phenacenes via Brønsted acid-mediated cyclization of
alkynyl biaryls, see: M. B. Goldfinger, K. B. Crawford, T. M. Swager, J.
Am. Chem. Soc. 1997, 119, 4578-4593.
[16] For construction of benzene rings via ring expansion of cyclopentene
moieties, see: K. Fuchibe, Y. Mayumi, N. Zhao, S. Watanabe, M.
Yokota, J. Ichikawa, Angew. Chem. 2013, 125, 7979-7982; Angew.
Chem. Int. Ed. 2013, 52, 7825-7828.
For selected reports on synthesis of PAHs via transition metal-
catalyzed cyclization of alkynylarenes, see: a) V. Mamane, P. Hannen,
A. Fürstner, Chem. Eur. J. 2004, 10, 4556-4575; b) H.-C. Shen, J.-M.
Tang, H.-K. Chang, C.-W. Yang, R.-S. Liu, J. Org. Chem. 2005, 70,
10113-10116; c) T.-A. Chen, T.-J. Lee, M.-Y. Lin, S. M. A. Sohel, E. W.-
G. Diau, S.-F. Lush, R.-S. Liu, Chem. Eur. J. 2010, 16, 1826-1833; d) T.
Matsuda, T. Moriya, T. Goya, M. Murakami, Chem. Lett. 2011, 40, 40-
41; e) K. Kitazawa, T. Kochi, M. Nitani, Y. Ie, Y. Aso, F. Kakiuchi, Chem.
Lett. 2011, 40, 300-302; f) C. Shu, C.-B. Chen, W.-X. Chen, L.-W. Ye,
Org. Lett. 2013, 15, 5542-5545; g) J. Carreras, G. Gopakumar, L. Gu, A.
Gimeno, P. Linowski, J. Petuškova, W. Thiel, M. Alcarazo, J. Am. Chem.
Soc. 2013, 135, 18815-18823.
[17] For reviews on triphenylene syntheses, see: a) D. Pérez, E. Guitián,
Chem. Soc. Rev. 2004, 33, 274-283; b) D. Pérez, D. Peña, E. Guitián,
Eur. J. Org. Chem. 2013, 5981-6013.
[18] For Brønsted acid-catalyzed cyclization of vinyl ethers, see: a) R. C.
Harvey, K. Lim, Q. Dai, J. Org. Chem. 2004, 69, 1372-1373; b) R. G.
Harvey, Q. Dai, C. Ran, T. M. Penning, J. Org. Chem. 2004, 69, 2024-
2032.
[19] For metal-catalyzed cyclization of vinyl ethers, see: a) K. Namba, H.
Yamamoto, I. Sasaki, K. Mori, H. Imagawa, M. Nishizawa, Org. Lett.
2008, 10, 1767-1770; b) M. Murai, N. Hosokawa, D. Roy, K. Takai, Org.
Lett. 2014, 16, 4134-4137.
[7]
[8]
a) C. K. Bradsher, J. Am. Chem. Soc. 1940, 62, 486-488; b) C. K.
Bradsher, W. J. Jackson, Jr., J. Am. Chem. Soc. 1954, 76, 734-738; c)
C. K. Bradsher, Chem. Rev. 1987, 87, 1277-1297, and references cited
therein; d) B. N. Diel, M. Han, P. L. Kole, D. B. Boaz, J. Label. Compd.
Radiopharm. 2007, 50, 551-553.
[20] For cycloaromatization of dioxolanes mediated by excess acids, see: a)
P. Bałczewski, M. Koprowski, A. Bodzioch, B. Marciniak, E. Różycka-
Sokołowska, J. Org. Chem. 2006, 71, 2899-2902; b) A. Bodzioch, B.
Marciniak, E. Różycka-Sokołowska, J. K. Jeszka, P. Uznański, S. Kania,
J. Kuliński, P. Bałczewski, Chem. Eur. J. 2012, 18, 4866-4876.
For the metal-catalyzed Bradsher reaction, see: Y. Kuninobu, T.
Tatsuzaki, T. Matsuki, K. Takai, J. Org. Chem. 2011, 76, 7005-7009.
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