Organic Letters
Letter
Y.; Yamamoto, T.; Ueda, K.; Kuroda, S.; Toste, F. D. J. Am. Chem. Soc.
2009, 131, 2809.
carbocycles and even spirocycles with alkylalkynes via C−C bond
formation on an inert C(sp3)−H bond. Theoretical study revealed
an interesting Cu-catalyzed concerted pathway of the C−C bond
formation.
(7) For reviews, see: (a) Yusubov, M. S.; Maskaev, A. V.; Zhdankin, V.
V. ARKIVOC 2011, No. i, 370. (b) Merritt, E. A.; Olofsson, B. Angew.
Chem., Int. Ed. 2009, 48, 9052. (c) Zhdankin, V. V.; Stang, P. J. Chem.
Rev. 2008, 108, 5299. (d) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002,
102, 2523. (e) Grushin, V. V. Chem. Soc. Rev. 2000, 29, 315. (f) Stang, P.
J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
(8) (a) Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013,
52, 5323. (b) Peng, J.; Chen, C.; Wang, Y.; Lou, Z.-B.; Li, M.; Xi, C.;
Chen, H. Angew. Chem., Int. Ed. 2013, 52, 7574. (c) Su, X.; Chen, C.;
Wang, Y.; Peng, J.; Lou, Z.-B.; Li, M. Chem. Commun. 2013, 49, 6752.
(d) Wang, Y.; Su, X.; Chen, C. Synlett 2013, 24, 2619.
ASSOCIATED CONTENT
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S
* Supporting Information
Experimental procedures, spectral data, computational details,
and results. This material is available free of charge via the
(9) (a) Suero, M. G.; Bayle, E. D.; Collins, B. S. L.; Gaunt, M. J. J. Am.
Chem. Soc. 2013, 135, 5332. (b) Walkinshaw, A. J.; Xu, W.-S.; Suero, M.
G.; Gaunt, M. J. J. Am. Chem. Soc. 2013, 135, 12532. (c) Copper-
catalyzed reactions between alkynes and diaryliodonium salts form
carbocyclic products was reported during the time this paper was
revisied: Zhang, F.; Das, S.; Walkinshaw, A. J.; Casitas, A.; Taylor, M.;
Suero, M. G.; Gaunt, M. J. J. Am. Chem. Soc. 2014, 136, 8851.
(10) (a) Couture, A.; Ho, K.; Hoshino, M.; Mayo, P.; Suau, R.; Ware,
W. R. J. Am. Chem. Soc. 1976, 98, 6218. (b) Somers, J. B. M.; Couture, A.;
Lablache-Combier, A.; Laarhoven, W. H. J. Am. Chem. Soc. 1985, 107,
1387. (c) Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1994, 116,
11570. (d) Xia, Y.; Liu, Z.-X.; Xia, Q.; Qu, P.-Y.; Ge, Y.; Zhang, Y.; Wang,
J.-B. Angew. Chem., Int. Ed. 2012, 51, 5714.
AUTHOR INFORMATION
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Corresponding Authors
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was supported by the National Natural Science
Foundation of China (21102080, 21372138, 21290194,
21221002, and 21032004) and Tsinghua University Initiative
Scientific Research Program (2011Z02150).
(11) (a) Yang, Y.-H.; Petersen, J. L.; Wang, K.-K. J. Org. Chem. 2003,
68, 5832. (b) Camps, P.; Domingo, L. R.; Formosa, X.; Galdeano, C.;
Gonal
J. Org. Chem. 2006, 71, 3464. (c) Wu, Y. G.; Zhang, J. Y.; Bo, Z. S. Org.
Lett. 2007, 9, 4435. (d) Sanchez-Larios, E.; Holmes, J. M.; Daschner, C.
́ ́
ez, D.; Munoz-Torrero, D.; Segales, S.; Font-Bardia, M.; Solans, X.
REFERENCES
■
́
(1) (a) Alberico, D.; Campeau, L. C.; Fagnou, K. Chem. Commun.
2006, 1253. (b) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew.
Chem., Int. Ed. 2009, 48, 5094. (c) Lyons, T. W.; Sanford, M. S. Chem.
Rev. 2010, 110, 1147. (d) Colby, D. A.; Bergman, R. G.; Ellman, J. A.
Chem. Rev. 2010, 110, 624. (e) Yeung, C. S.; Dong, V. M. Chem. Rev.
2011, 111, 1215. (f) Wencle-Dlord, J.; Droge, T.; Liu, F.; Glorius, F.
Chem. Soc. Rev. 2011, 40, 4740.
(2) (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
(b) Davies, H. M. L. Angew. Chem., Int. Ed. 2006, 45, 6422. (c) Godula,
K.; Sames, D. Science 2009, 312, 67. (d) Doyle, M. P.; Duffy, R.;
Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704. (e) Baudoin, O.
Chem. Soc. Rev. 2011, 40, 4902. (f) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem.
Rev. 2011, 111, 1293. (g) Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol.
2011, 1, 191.
(3) (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am.
Chem. Soc. 2005, 127, 7330. (b) Li, Z.-P.; Li, C.-J. J. Am. Chem. Soc. 2005,
128, 56. (c) Yin, G.; Wu, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 11978.
(d) Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036.
(e) Xie, P.; Xie, Y.; Qian, B.; Zhou, H.; Xia, C.; Huang, H. J. Am. Chem.
Soc. 2012, 134, 9902.
(4) (a) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004,
126, 9542. (b) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc.
2006, 128, 12634. (c) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc.
2010, 132, 3965. (d) Stowers, K. J.; Fortner, K. C.; Sanford, M. S. J. Am.
Chem. Soc. 2011, 133, 6541. (e) Qian, B.; Xie, P.; Xie, Y.-J.; Huang, H.-
M. Org. Lett. 2011, 13, 2580. (f) Nadres, E. T.; Daugulis, O. J. Am. Chem.
Soc. 2012, 134, 7. (g) Pan, F.; Shen, P.-X.; Zhang, L.-S.; Wang, X.; Shi,
Z.-J. Org. Lett. 2013, 15, 4758.
L.; Gravel, M. Org. Lett. 2010, 12, 5772. (e) Singh, C.; Hassam, M.;
Naikade, N. K.; Verma, V. P.; Singh, A. S.; Puri, S. K. J. Med. Chem. 2010,
53, 7587.
(12) (a) Ren, P.; Stern, L.-A.; Hu, X.-L. Angew. Chem., Int. Ed. 2012, 51,
9110. (b) Yang, C.-T.; Zhang, Z.-Q.; Liang, J.; Liu, J.-H.; Lu, X.-Y.; Chen,
H.-H.; Liu, L. J. Am. Chem. Soc. 2012, 134, 11124.
(13) (a) Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.; Gaunt,
M. J. J. Am. Chem. Soc. 2012, 134, 10773. (b) Chen, B.; Hou, X.-L.; Li, Y.-
X.; Wu, Y.-D. J. Am. Chem. Soc. 2011, 133, 7668. (c) Xiao, B.; Fu, Y.; Xu,
J.; Gong, T.-J.; Dai, J.-J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468.
(d) Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593. (e) Phipps, R. J.;
Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
(14) (a) Biermann, U.; Koch, R.; Metzger, J. O. Angew. Chem., Int. Ed.
2006, 45, 3076. (b) Kanishchev, M. I.; Shegolev, A. A.; Smit, W. A.;
Caple, R.; Kelner, M. J. J. Am. Chem. Soc. 1979, 101, 5660. (c) Schegolev,
A. A.; Smit, W. A.; Kucherov, V. F.; Caple, R. J. Am. Chem. Soc. 1975, 97,
6604.
(15) The KIE experiment was carried out with 5D-1a and 2a. After the
majority of 5D-1a was converted, the mixture of 3a and D-3a was
isolated at a ratio around 7:3. The deuterium of D-3a is located at the
allylic position and may be exchanged by protons in the reaction system.
Therefore, this KIE result is not sufficient to reveal the process of
cylization.
(16) This mechanism of pathway A is similar to that proposed in ref
14a, but the role of Cu catalyst cannot be neglected as caculated.
(17) Talele, H. R.; Gohil, M. J.; Bedekar, A. V. Bull. Chem. Soc. Jpn.
2009, 82, 1182. (b) Rahmahan, A. U.; Vuano, B. J. Org. Chem. 1969, 34,
763.
(5) (a) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.;
Murai, S. J. Am. Chem. Soc. 2001, 123, 10935. (b) Li, Z.-P.; Li, C.-J. J. Am.
Chem. Soc. 2004, 126, 11810. (c) Li, Z.-P.; Li, C.-J. J. Am. Chem. Soc.
2005, 127, 3672. (d) Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069.
(e) Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128,
́
14220. (f) Basle, O.; Li, C.-J. Org. Lett. 2008, 10, 3661.
(g) Kumaraswamy, G.; Murthy, A. N.; Pitchaiah, A. J. Org. Chem.
2010, 75, 3916. (h) Gogoi, A.; Guin, S.; Rout, S. K.; Patel, B. K. Org. Lett.
2013, 15, 1802.
(6) (a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
(b) Bhunia, S.; Liu, R.-S. J. Am. Chem. Soc. 2008, 130, 16488. (c) Horino,
D
dx.doi.org/10.1021/ol501655g | Org. Lett. XXXX, XXX, XXX−XXX