Communication
ChemComm
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17, 9586; (h) A.-H. Garcıa-Munoz, M. Tomas-Gamasa, M. C. Perez-
(10351064101000000), and the Program for New Century Excellent
Talents in Universities (NCET-12-0189).
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Aguilar, E. Cuevas-Yanez and C. Valdes, Eur. J. Org. Chem., 2012, 3925.
7 Reviews: (a) Q. Xiao, Y. Zhang and J. Wang, Acc. Chem. Res., 2013,
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46, 236; (b) J. Barluenga and C. Valdes, Angew. Chem., Int. Ed., 2011,
50, 7486; (c) X. Zhao, Y. Zhang and J. Wang, Chem. Commun., 2012,
48, 10162; (d) Z. Shao and H. Zhang, Chem. Soc. Rev., 2012, 41, 560;
(e) Z. Liu and J. Wang, J. Org. Chem., 2013, 78, 10024; ( f ) Y. Xia,
Y. Zhang and J. Wang, ACS Catal., 2013, 3, 2586.
8 For selected recent examples: (a) X. Zeng, G. Cheng, J. Shen and
X. Cui, Org. Lett., 2013, 15, 3022; (b) Q. Xiao, B. Wang, L. Tian,
Y. Yang, J. Ma, Y. Zhang, S. Chen and J. Wang, Angew. Chem., Int.
Notes and references
1 (a) M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods
for Organic Synthesis with Diazo Compounds: From Cyclopropanes
to Ylides, Wiley-Interscience, New York, 1998; (b) F. Z. Dorwald,
Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999;
(c) Metal Carbenes in Organic Synthesis, Topics in Organometallic
¨
¨
´
Ed., 2013, 52, 9305; (c) L. Florentino, F. Aznar and C. Valdes, Org.
˜
Lett., 2012, 14, 2323; (d) J. Barluenga, N. Quinones, M.-P. Cabal,
Chemistry, ed. K. H. Dotz, Springer-Verlag, Berling, 2004, vol. 13;
(d) M. P. Doyle and D. C. Forbes, Chem. Rev., 1998, 98, 911; A. Padwa
and M. D. Weingarten, Chem. Rev., 1996, 96, 223; (e) T. Ye and
M. A. McKervey, Chem. Rev., 1994, 94, 1091.
´
F. Aznar and C. Valdes, Angew. Chem., Int. Ed., 2011, 50, 2350;
´
(e) J. Barluenga, L. Florentino, F. Aznar and C. Valdes, Org. Lett.,
´
2011, 13, 510; ( f ) J. Barluenga, M. Tomas-Gamasa, F. Aznar and
2 For reviews and selected examples, see: (a) L. D. Shirtcliff,
S. P. McClintock and M. M. Haley, Chem. Soc. Rev., 2008, 37, 343;
(b) R. S. Sheridan, Chem. Rev., 2013, 113, 7179; (c) C. R. Pharr,
L. A. Kopff, B. Bennett, S. A. Reid and R. J. McMahon, J. Am. Chem.
´
C. Valdes, Adv. Synth. Catal., 2010, 352, 3235; (g) J. Barluenga,
´
M. Escribano, F. Aznar and C. Valdes, Angew. Chem., Int. Ed., 2010,
´
49, 6856; (h) J. Barluenga, M. Tomas-Gamasa, F. Aznar and
¨
´
C. Valdes, Chem. – Eur. J., 2010, 16, 12801; (i) J. Barluenga,
Soc., 2012, 134, 6443; (d) C. Roser, R. Albers and W. Sander, Eur.
´
J. Org. Chem., 2001, 269; (e) R. V. Hoffman and H. Shechter, J. Am.
Chem. Soc., 1978, 100, 7934; ( f ) R. V. Hoffman, G. G. Orphanides
and H. Shechter, J. Am. Chem. Soc., 1978, 100, 7927; (g) R. V.
Hoffman and H. Shechter, J. Org. Chem., 1974, 39, 2939; (h) R. V.
Hoffman and H. Shechter, J. Am. Chem. Soc., 1971, 93, 5940.
3 (a) M. J. Gonzalez, E. Lopez and R. Vicente, Chem. Commun., 2014,
50, 5379; (b) F. Hu, Y. Xia, C. Ma, Y. Zhang and J. Wang, Org. Lett.,
2014, 16, 4082; (c) M. J. Gonzalez, L. A. Lopez and R. Vicente, Org.
Lett., 2014, 16, 5780; (d) J. Ma, H. Jiang and S. Zhu, Org. Lett., 2014,
16, 4472; (e) Y. Xia, S. Qu, Q. Xiao, Z.-X. Wang, P. Qu, L. Chen, Z. Liu,
L. Tian, Z. Huang, Y. Zhang and J. Wang, J. Am. Chem. Soc., 2013,
M. Escribano, P. Moriel, F. Aznar and C. Valdes, Chem. – Eur. J.,
2009, 15, 13291; ( j) Q. Xiao, J. Ma, Y. Yang, Y. Zhang and J. Wang,
´
Org. Lett., 2009, 11, 4732; (k) J. Barluenga, M. Tomas-Gamasa,
´
P. Moriel, F. Aznar and C. Valdes, Chem. – Eur. J., 2008, 14, 4792.
9 (a) R. Kudirka, S. K. J. Devine, C. S. Adams and D. L. Van Vranken,
Angew. Chem., Int. Ed., 2009, 48, 3677; (b) L. Zhou, F. Ye, Y. Zhang
and J. Wang, J. Am. Chem. Soc., 2010, 132, 13590; (c) A. Khanna,
C. Maung, K. R. Johnson, T. T. Luong and D. L. Van Vranken, Org.
Lett., 2012, 14, 3233; (d) P.-X. Zhou, J.-Y. Luo, L.-B. Zhao, Y.-Y. Ye and
Y.-M. Liang, Chem. Commun., 2013, 49, 3254; (e) P.-X. Zhou, Y.-Y. Ye
and Y.-M. Liang, Org. Lett., 2013, 15, 5080; ( f ) Y.-Y. Ye, P.-X. Zhou,
J.-Y. Luo, M.-J. Zhong and Y.-M. Liang, Chem. Commun., 2013,
49, 10190.
´
´
´
´
´
´
135, 13502; ( f ) J. Gonzalez, J. Gonzalez, C. Perez-Calleja, L. A. Lopez
and R. Vicente, Angew. Chem., Int. Ed., 2013, 52, 5853; (g) M. Xu,
T.-T. Ren, K.-B. Wang and C.-Y. Li, Adv. Synth. Catal., 2013, 10 B. Yin, X. Zhang, J. Liu, X. Li and H. Jiang, Chem. Commun., 2014,
´
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355, 2488; (h) R. Vicente, J. Gonzalez, L. Riesgo, J. Gonzalez and
50, 8113.
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L. A. Lopez, Angew. Chem., Int. Ed., 2012, 51, 8063; (i) J. Barluenga, 11 For related examples: (a) Y. Shi, P. Brenner, S. Bertsch, K. Radacki
´
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L. Riesgo, R. Vicente, L. A. Lopez and M. Tomas, J. Am. Chem. Soc.,
2008, 130, 13528; ( j) Y. Kato, K. Miki, F. Nishino, K. Ohe and
S. Uemura, Org. Lett., 2003, 5, 2619; (k) K. Miki, T. Yokoi, F. Nishino,
and R. D. Dewhurst, Organometallics, 2012, 31, 5599; (b) R. D. Dewhurst,
¨
R. Muller, M. Kaupp, K. Radacki and K. Gotz, Organometallics, 2010,
29, 4431.
Y. Kato, Y. Washitake, K. Ohe and S. Uemura, J. Org. Chem., 2004, 12 For recent examples concerning synthesis of indoles from orth-
69, 1557; (l) K. Miki, Y. Washitake, K. Ohe and S. Uemura, Angew.
Chem., Int. Ed., 2004, 43, 1857; (m) K. Miki, F. Nishino, K. Ohe and
S. Uemura, J. Am. Chem. Soc., 2002, 124, 5260.
4 For reviews concerning synthetic application of furans, see:
(a) B. H. Lipshutz, Chem. Rev., 1986, 86, 795; (b) F. W.
Lichtenthaler, Acc. Chem. Res., 2002, 35, 728; (c) A. A. Rosatella,
S. P. Simeonov, R. F. M. Frade and C. A. M. Afonso, Green Chem.,
2011, 13, 754; (d) P. Gallezot, Chem. Soc. Rev., 2012, 41, 1538;
(e) R. J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra,
H. J. Heeres and J. G. de Vries, Chem. Rev., 2013, 113, 1499.
substituted benzylfurans under acidic conditions, see: (a) V. T.
Abaev, A. T. Plieva, P. N. Chalikidi, M. G. Uchuskin, I. V. Trushkov
and A. V. Butin, Org. Lett., 2014, 16, 4150; (b) M. G. Uchuskin,
N. V. Molodtsova, S. A. Lysenko, V. N. Strel’nikov, I. V. Trushkov and
A. V. Butin, Eur. J. Org. Chem., 2014, 2508; (c) A. Kuznetsov,
A. Makarov, A. E. Rubtsov, A. V. Butin and V. Gevorgyan, J. Org.
Chem., 2013, 78, 12144; (d) M. G. Uchuskin, N. V. Molodtsova,
V. T. Abaev, I. V. Trushkov and A. V. Butin, Tetrahedron, 2012,
68, 4252; (e) A. V. Butin, S. K. Smirnov, F. A. Tsiunchik, M. G.
Uchuskin and I. V. Trushkov, Synthesis, 2008, 2943; ( f ) A. V. Butin,
S. K. Smirnov and I. V. Trushkov, Tetrahedron Lett., 2008, 49, 20.
5 For recent examples of furan dearomatization in our group, see:
(a) B.-L. Yin, J.-Q. Lai, Z.-R. Zhang and H.-F. Jiang, Adv. Synth. Catal., 13 R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689.
2011, 353, 1961; (b) B. Yin, G. Zeng, C. Cai, F. Ji, L. Huang, Z. Li and 14 For similar elimination reactions to form allene, see: (a) K. Takanishi,
H. Jiang, Org. Lett., 2012, 14, 616; (c) B. Yin, C. Cai, G. Zeng,
R. Zhang, X. Li and H. Jiang, Org. Lett., 2012, 14, 1098; (d) B. Yin,
L. Huang, X. Wang, J. Liu and H. Jiang, Adv. Synth. Catal., 2013,
355, 370; (e) L. Huang, X. Zhang, J. Li, K. Ding, X. Li, W. Zheng and
B. Yin, Eur. J. Org. Chem., 2014, 338; ( f ) X. Zhang, L. Huang, H. Peng,
F. Ji, X. Li and B. Yin, Tetrahedron, 2014, 70, 5242; (g) B. Yin, H. Yu,
H. Urabe and I. Kuwajima, Tetrahedron Lett., 1987, 28, 2281;
(b) K. Isao, H. Showay, T. Toshihiko and S. Makoto, Tetrahedron Lett.,
1980, 21, 3209. Other mechanisms for this step cannot be ruled out at
this stage. For example, an intramolecular nucleophilic dearomatiza-
tion to form a six-membered ring followed by migration of the amine
group is a possibility.
Z. Li, W. Zhong and W. Gu, Synthesis, 2012, 3735; (h) H. Yu, 15 For examples of the transformation of o-allenylaniline into indoles,
W. Zhong, T. He, W. Gu and B. Yin, Tetrahedron Lett., 2013,
54, 1256; (i) B.-L. Yin, J.-Q. Lai, L. Huang, X.-Y. Zhang and F.-H. Ji,
Synthesis, 2012, 2567.
see: (a) A. Saito, A. Kanno and Y. Hanzawa, Angew. Chem., Int. Ed.,
2007, 46, 3931; (b) F. Inagaki, M. Mizutani, N. Kuroda and C. Mukai,
J. Org. Chem., 2009, 74, 6402; (c) C. Mukai and Y. Takahashi, Org.
Lett., 2005, 7, 5793.
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6 For selected recent examples: (a) J. Barluenga, M. Tomas-Gamasa,
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F. Aznar and C. Valdes, Angew. Chem., Int. Ed., 2010, 49, 4993; 16 For reviews concerning the application and synthesis of benzothio-
(b) X. Creary, J. Am. Chem. Soc., 2013, 135, 6570; (c) J.-B. Liu, H. Yan
and G. Lu, Tetrahedron Lett., 2013, 54, 891; (d) Q. Sha and Y. Wei,
Tetrahedron, 2013, 69, 3829; (e) Q. Ding, B. Cao, J. Yuan, X. Liu and
Y. Peng, Org. Biomol. Chem., 2011, 9, 748; ( f ) Q. Sha and Y.-Y. Wei,
Org. Biomol. Chem., 2013, 11, 5615; (g) H. E. Bartrum, D. C.
Blakemore, C. J. Moody and C. J. Hayes, Chem. – Eur. J., 2011,
phenes, see: (a) Handbook of Thiophene-Based Materials, ed. I. F.
Perepichka and D. F. Perepichka, Wiley-VCH Verlag, New York, 2009;
(b) D. A. Horton, G. T. Bourne and M. L. Smythe, Chem. Rev., 2003,
103, 893; (c) T. Y. Zhang, J. O’Toole and C. S. Proctor, Sulfur Rep., 1999,
22, 1; (d) B. Godoi, R. F. Schumacher and G. Zeni, Chem. Rev., 2011,
111, 2937; (e) T. W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110, 1147.
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