Cu2O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases
- Corresponding author: Zeng Xianghua, xianghuazeng@mail.zjxu.edu.cn
Citation:
Ma Nan, Zeng Xianghua. Cu2O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases[J]. Chinese Journal of Organic Chemistry,
;2018, 38(6): 1556-1561.
doi:
10.6023/cjoc201712038
(a) Lerch, M. L. ; Harper, M. K. ; Faulkner, D. J. J. Nat. Prod. 2003, 66, 667.
(b) Lechner, D. ; Stavri, M. ; Oluwatuyi, M. ; Perda-Miranda, R. ; Gibbons, S. Phytochemistry 2004, 65, 331.
(c) Constable, C. P. ; Towers, G. H. N. Planta Med. 1989, 55, 35.
(d) Zhou, Y. Z. ; Ma, H. Y. ; Chen, H. ; Qiao, L. ; Yao, Y. ; Cao, J. Q. ; Pei, Y. H. Chem. Pharm. Bull. 2006, 54, 1455.
(e) Ladika, M. ; Fisk, T. E. ; Wu, W. W. ; Jons, S. D. J. Am. Chem. Soc. 1994, 116, 12093.
(f) Mayer, S. F. ; Steinreiber, A. ; Orru, R. V. A. ; Faber, K. J. Org. Chem. 2002, 67, 9115.
(g) Zeni, G. ; Panatieri, R. B. ; Lissner, E. ; Menezes, P. H. ; Braga, A. L. ; Stefani, H. A. Org. Lett. 2001, 3, 819.
(h) Stüts, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320.
(a) Gholami, M. ; Tykwinski, R. R. Chem. Rev. 2006, 106, 4997.
(b) Baxter, P. N. W. ; Dali-Youcef, R. J. Org. Chem. 2005, 70, 4935.
(c) Marsden, J. A. ; Haley, M. M. J. Org. Chem. 2005, 70, 10213.
(a) Cataldo, F. In Polyynes: Synthesis Properties, and Applications, CRC Press/Taylor & Francis, Boca Raton, Florida, 2005.
(b) Diederich, F. ; Stang, P. J. ; Tykwinski, R. R. Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2005.
Crowley, J. D.; Goldup, S. M.; Lee, A. L.; Leigh, D. A.; McBurney, R. T. Chem.Soc.Rev. 2009, 38, 1530.
doi: 10.1039/b804243h
Glaser, C. Ber.Dtsch.Chem.Ges. 1869, 2, 422.
doi: 10.1002/(ISSN)1099-0682
Chen, L.; Lemma, B. E.; Rich, J. S.; Mack, J. Green Chem. 2014, 16, 1101.
doi: 10.1039/C3GC41847B
Mo, G.; Tian, Z.; Li, J.; Wen, G.; Yang, X. Appl. Organomet.Chem. 2015, 29, 231.
doi: 10.1002/aoc.v29.4
(a) Leyva-Pérez, A. ; Doménech, A. ; Al-Resayes, S. I. ; Corma, A. ACS Catal. 2012, 2, 121.
(b) Peng, H. ; Xi, Y. ; Ronaghi, N. ; Dong, B. ; Akhmedov, G. N. ; Shi, X. J. Am. Chem. Soc. 2014, 136, 13174.
(a) Fan, X. ; Li, N. ; Shen, T. ; Cui, X. -M. ; Lv, H. ; Zhu, H. -B. ; Guan, Y. -H. Tetrahedron 2014, 70, 256.
(b) Yin, K. ; Li, C. -J. ; Li, J. ; Jia, X. -S. Appl. Organomet. Chem. 2011, 25, 16.
(c) Navale, B. S. ; Bhat, R. G. RSC Adv. 2013, 3, 5220.
(d) Zhang, S. ; Liu, X. ; Wang, T. Adv. Synth. Catal. 2011, 353, 1463.
(e) Jia, X. ; Yin, K. ; Li, C. ; Li, J. ; Bian, H. Green Chem. 2011, 13, 2175.
(f) Balaraman, K. ; Kesavan, V. Synthesis 2010, 3461.
(g) Kusuda, A. ; Xu, X. -F. ; Wang, X. ; Tokunaga, E. ; Shibata, N. Green Chem. 2011, 13, 843.
(h) Adimurthy, S. ; Malakar, C. C. ; Beifuss, U. J. Org. Chem. 2009, 74, 5648.
(i) Yin, K. ; Li, C. ; Li, J. ; Jia, X. Green Chem. 2011, 13, 591.
(j) Wang, D. ; Li, J. ; Li, N. ; Gao, T. ; Hou, S. ; Chen, B. Green Chem. 2010, 12, 45.
(k) Kabalka, G. W. ; Wang, L. ; Pagni, R. M. Synlett 2001, 108.
(l) Li, Y. -N. ; Wang, J. -L. ; He, L. -N. Tetrahedron Lett. 2011, 52, 3485.
(m) Sagadevan, A. ; Charpe, V. P. ; Hwang, K. C. Catal. Sci. Technol. 2016, 6, 7688.
(n)Sagadevan, A. ; Lyu, P. -C. ; Hwang, K. C. Green Chem. 2016, 18, 4526.
(o) Oishi, T. ; Katayama, T. ; Yamaguchi, K. ; Mizuno, N. Chem. Eur. J. 2009, 15, 7539.
(p) Oishi, T. ; Yamaguchi, K. ; Mizuno, N. ACS Catal. 2011, 1, 1351.
(q) Zhu, Y. ; Shi, Y. Org. Biomol. Chem. 2013, 11, 7451.
(r) Kamata, K. ; Yamaguchi, S. ; Kotani, M. ; Yamaguchi, K. ; Mizuno, N. Angew. Chem., Int. Ed. 2008, 47, 2407.
Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski, M. C. Chem.Rev. 2013, 113, 6234.
doi: 10.1021/cr300527g
Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org.Lett. 2009, 11, 709.
doi: 10.1021/ol8027863
Ye, R.; Zhukhovitskiy, A. V.; Deraedt, C. V.; Toste, F. D.; Somorjai, G. A. Acc.Chem.Res. 2017, 50, 1894.
doi: 10.1021/acs.accounts.7b00232
Tang, B.-X.; Fang, X.-N.; Kuang, R.-Y.; Wu, J.-H.; Chen, Q.; Hu, S.-J.; Liu, Y.-L. Appl.Organomet.Chem. 2016, 30, 943.
doi: 10.1002/aoc.v30.11
Su, L.; Dong, J.; Liu, H.; Sun, M.; Qiu, R.; Zhou, Y.; Yin, S.-F. J. Am.Chem.Soc. 2016, 138, 12348.
doi: 10.1021/jacs.6b07984
Xu, H.; Wu, K.; Tian, J.; Zhu, L.; Yao, X. Green Chem. 2018, 20, 793.
doi: 10.1039/C7GC03120C
Theunissen, C.; Evano, G. Org.Lett. 2014, 16, 4488.
doi: 10.1021/ol502030y
Chinchilla, R.; Najera, C. Chem.Soc.Rev. 2011, 40, 5084.
doi: 10.1039/c1cs15071e
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