ChemComm
Page 4 of 4
Journal Name
COMMUNICATION
Soc., 2005, 127, 16468; J. P. Wolfe and M. A. Rossi, J. Am. Chem.
DOI: 10.1039/C4CC08363F
Chem., 2005, 70, 3099; A. F. Ward and J. P. Wolfe, Org.Lett., 2009,
11, 2209.
6
For reviews about diaryliodonium salts, see: M. S. Yusubov, A. V.
Maskaev and V. V. Zhdankin, ARKIVOC 2011, (i), 370; E. A.
Merritt and B. Olofsson, Angew. Chem. Int. Ed., 2009, 48, 9052; V.
V. Zhdankin and P. J. Stang, Chem. Rev., 2008, 108, 5299; V. V.
Zhdankin and P. J. Stang, Chem. Rev., 2002, 102, 2523; V. V.
Grushin, Chem. Soc. Rev., 2000, 29, 315; P. J. Stang and V. V.
Zhdankin, Chem. Rev., 1996, 96, 1123.
Conclusions
In summary, we reported
a
novel Cu-catalyzed
intramolecular aryl-etherification reaction of alkoxyl alkynes
with diaryliodonium salts. The reactions proceed smoothly to
give useful oxo-heterocycles with readily available linear
starting materials via cleavage of a stable C-O bond.
7
Y. Wang, C. Chen, J. Peng and M. Li, Angew. Chem., Int. Ed., 2013,
52, 5323; J. Peng, C. Chen, Y. Wang, Z.-B. Lou, M Li. C. Xi and H.
Chen, Angew. Chem., Int. Ed. 2013, 52, 7574; X. Su, C. Chen, Y.
Notes and references
Wang, J. Peng, Z.-B. Lou and M. Li, Chem. Commun., 2013, 49
6752; Y. Wang, X. Su and C. Chen, Synlett, 2013, 24, 2619.
,
a
Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical
Biology (Ministry of Education), Department of Chemistry, Tsinghua
University, Beijing 100084, China
8
9
A. J. Walkinshaw, W.-S. Xu, M. G. Suero and M. J. Gaunt. J. Am.
Chem. Soc., 2013, 135, 12532; E. Cahard, N. Bremeyer and M. J.
Gaunt. Angew. Chem., Int. Ed., 2013, 52, 9284; N. T. Vo, R. D. M.
Pace, F. O’Har a and M. J. Gaunt, J. Am. Chem. Soc., 2008, 130, 404.
C. Yu, O. H. Jamison and F. Timothy, Angew. Chem., Int. Ed., 2008,
47, 1893; C. Patrick and M. Bernard. Tetrahedron Letters, 1977, 17,
1493.
b
Key Laboratory of Systems Bioengineering, Ministry of Education,
Department of Pharmaceutical Engineering, School of Chemical
Engineering and Technology, Tianjin University, Tianjin 300072, China.
† This work was supported by National Natural Science Foundation of
China (21102080, 21372138) and Tsinghua University Initiative
Scientific Research Program (2011Z02150). Electronic supplementary
10 L. V. Yudanov, A. V. Matveev, K. M. Neyman and N. Rosch. J. Am.
Chem. Soc., 2008, 130, 9342; J. M. Nichols, L. M. Bishop, R. G.
Bergman and J. A. Ellman, J. Am. Chem. Soc.,2010, 132, 12554; Y.-
G. Zhao and V. Snieckus. J. Am. Chem. Soc., 2014, 136, 11224; D.-Y.
Yu and Z.-J. Shi. Angew. Chem., Int. Ed., 2011, 50, 7097.
11 R. Ghosh and B. Olofsson. Org. Lett., 2014, 16, 1830; E. Lindstedt,
R. Ghosh and B. Olofsson, Org. Lett., 2013, 15, 6070.
1
Information (ESI) available: Full experimental details, including H and
13C NMR data of new compounds For ESI and crystallographic data in
CIF (CCDC 1019497) of 3af see DOI: 10.1039/c000000x/
1
For reviews, see: T. L. B. Boivin, Tetrahedron, 1987, 43, 3309; G.
Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321; K. E. Harding
and T. H. Tiner, Comp. Org. Synh., 1991, 4, 363; G. Rousseau and F.
12 CCDC number: 1019497. The single crystal suitable for XRD was
obtained by slow evaporation its solution in n-hexane.
Homsi, Chem. Soc. ReV., 1997, 26, 453; S. Robin and G. Rousseau,
Tetrahedron, 1998, 54, 13681; S. Robin and G. Rousseau, Eur. J.
Org. Chem., 2002, 3099; S. Ranganathan, K. M. Muraleedharan, N.
K. Vaish and N. Jayaraman. Tetrahedron, 2004, 60, 5273; A. N.
French, S. Bissmire and T. Wirth, Chem. Soc. Rev., 2004, 33, 354; Y.
Tang, J. Oppenheimer, Z. Song, L. You, X. Zhang and R. P. Hsung,
Tetrahedron, 2006, 62, 10785; A. M. Montana, C. Batalla and J. A.
Barcia Curr. Org. Chem., 2009, 13, 919.
13 S. Mandal, K. N. Parida, S. Samanta and J. N. Moorthy, J. Org.
Chem. Soc., 2011, 76, 7406.
14 Selected examples: J. Peng, C. Chen, J. Chen, X. Su, C. Xi,, H. Chen,
Org. Lett., 2014, 16, 3776; R. J. Phipps, L. McMurray, S. Ritter, H. A.
Duong and M. J. Gaunt, J. Am. Chem. Soc., 2012, 134, 10773; B.
Chen, X.-L. Hou, Y.-X. Li and Y.-D. Wu, J. Am. Chem. Soc., 2011,
133, 7668; B. Xiao, Y. Fu, J. Xu, T.-J. Gong, J.-J. Dai, J. Yi and L.
Liu, J. Am. Chem. Soc., 2010, 132, 468; R. J. Phipps and M. J. Gaunt,
Science, 2009, 323, 1593; R. J. Phipps, N. P. Grimster and M. J.
Gaunt, J. Am. Chem. Soc., 2008, 130, 8172. Other metal such as Pd-
catalyzed reaction of alkynes with diaryliodonium salts: S. Tang, P.
Peng, P, Zhong, J.-H. Li, J. Org. Chem., 2008, 73, 5476.
2
Selective examples: G.A. Sotzing, J. R. Reynolds and P. J. Steel,
Chem. Mater., 1996, 8, 882; M. F. Pepitone, S. S. Hardaker and R. V.
Gregory, Chem. Mater., 2003, 15, 557; C.-F. Lee, L.-M. Yang, T.-Y.
Hwu, A.-S. Feng, J.-C. Tseng and T.-Y. Luh, J. Am. Chem.
Soc.,2000. 122, 4992; H. Chen, W. Delaunay, J. Li, Z. Wang, P.-A.
Bouit, D. Tondelier, B. Geffroy, F. Mathey, Z. Duan, R. Réau and M.
Hissler, Org. Lett., 2013, 15, 330.
15 H. R. Talele, M. J. Gohil and A. V. Bedekar, Bull. Chem. Soc. Jpn.,
2009, 82, 1182; A. U. Rahmahan and B. Vuano, J. Org. Chem., 1969,
34, 763.
3
Selective examples: F. Q. Alali, X.-X. Liu and J. L. McLaughlin. J.
Nat. Prod., 1999, 62, 504; M. C. Zafra- Polo, B Figadere, T Gallardo,
J. R. Tormo and D Cortes, Phytochemistry, 1998, 48, 1087; H. C.
Shen, Tetrahedron, 2009, 65, 3931.
16 Y. M. A. Yamada, Y. Yuyama, T. Sato, S. Fujikawa and Y. Uozumi,
Angew. Chem., Int. Ed., 2014, 53, 127.
17 W. Ernest, E. L. Michelott, C. S. Swindell and M. Tingoli, J. Org.
Chem., 1984, 49, 4894.
4
5
Selective examples: F. J. Urban and B. S. Moore, J. Heterocycl.
Chem., 1992, 29, 431 and references cited therein; K. W. Hunt, J. P.
Rizzi and A. Cook, PCT Int. Appl., WO 2011072064A1, 2011.
For reviews, see: J. P. Wolfe, Eur. J. Org. Chem., 2007, 571; J. P.
Wolfe, Synlett, 2008, 2913; M. B. Hay and J. P. Wolfe, J. Am. Chem.
18 A. B. Foster, M. Jarman, O. Leung, R. Molague, G. Leclercq and N.
Devleeschouwer. J. Med. Chem., 1985, 28, 1491; L.-P. Wang, L. O.
Miller, R. T. Nolte, D. P. McDonnell, T. M. Willson and W. J.
Zuercher, Bioorg. Med. Chem. Lett., 2006, 16, 821.
4 | J. Name., 2012, 00, 1‐3
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