Copyright (c) 2022 AJC
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CuI/TMEDA Catalyzed Solvent Free Homo-Coupling Reaction of Terminal Alkynes towards the Synthesis of Buta-1,3-diynes
Corresponding Author(s) : Sudhir K. Sharma
Asian Journal of Chemistry,
Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022
Abstract
An efficient method for the synthesis of buta-1,3-diynes have been developed via copper(I) catalyzed homocoupling reaction of terminal acetylenes in presence of CuI and tetramethylethylenediamine (TMEDA) at 100 ºC for 3.0 h under solvent-free conditions. This efficient methodology allowed the homocoupling of five terminal alkynes in moderate to excellent yields.
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- S. Gupta, S.K. Sharma, A.K. Mandadapu, H.M. Gauniyal and B. Kundu, Tetrahedron Lett., 52, 4288 (2011); https://doi.org/10.1016/j.tetlet.2011.06.021
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- S.K. Sharma, Adv. Org. Chem. Lett., 4, 1 (2017).
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- A.L.K. Shi Shun and R.R. Tykwinski, Angew. Chem. Int. Ed., 45, 1034 (2006); https://doi.org/10.1002/anie.200502071
- F. Bohlmano, T. Burkhardt and C. Zdero, Naturally Occurring Acetylenes; Academic Press: London (1973).
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- E. Valenti, M.A. Pericàs and F. Serratosa, J. Am. Chem. Soc., 112, 7405 (1990); https://doi.org/10.1021/ja00176a056
- P. Cadiot and W. Chodkiewicz, Eds.: H.G. Viehe, In Chemistry of Acetylenes, Marcel Dekker: New York, pp 597 (1969).
- G. Engliton and A.R. Galbraith, Chem. Ind., 737 (1956).
- Q. Sun, Z. Lv, Y. Du, Q. Wu, L. Wang, L. Zhu, X. Meng, W. Chen and F.-S. Xiao, Chem. Asian J., 8, 2822 (2013); https://doi.org/10.1002/asia.201300690
- A.S. Hay, J. Org. Chem., 27, 3320 (1962); https://doi.org/10.1021/jo01056a511
- D. Wang, J. Li, N. Li, T. Gao, S. Hou and B. Chen, Green Chem., 12, 45 (2010); https://doi.org/10.1039/B917448F
- K. Yin, C. Li, J. Li and X. Jia, Green Chem., 13, 591 (2011); https://doi.org/10.1039/c0gc00413h
- L. Bettanin, G.V. Botteselle, M. Godoi and A.L. Braga, Green Chem. Lett. Rev., 7, 105 (2014); https://doi.org/10.1080/17518253.2014.895868
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References
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J. Li, Y. Xu, X. Hu, S. Zhu and L. Liu, Org. Lett., 22, 9478 (2020); https://doi.org/10.1021/acs.orglett.0c03451
G. Huang, J. Li, J. Li, J. Li, M. Sun, P. Zhou, L. Chen, Y. Huang, S. Jiang and Y. Li, J. Org. Chem., 85, 13037 (2020); https://doi.org/10.1021/acs.joc.0c01733
S.K. Sharma, A.K. Mandadapu, B. Kumar and B. Kundu, J. Org. Chem., 76, 6798 (2011); https://doi.org/10.1021/jo201228t
S.K. Sharma, S. Gupta, M. Saifuddin, A.K. Mandadapu, P.K. Agarwal, H.M. Gauniyal and B. Kundu, Tetrahedron Lett., 52, 65 (2011); https://doi.org/10.1016/j.tetlet.2010.10.147
S. Gupta, S.K. Sharma, A.K. Mandadapu, H.M. Gauniyal and B. Kundu, Tetrahedron Lett., 52, 4288 (2011); https://doi.org/10.1016/j.tetlet.2011.06.021
S.K. Sharma, A.K. Mandadapu, M. Saifuddin, S. Gupta, P.K. Agarwal, A.K. Mandwal, H.M. Gauniyal and B. Kundu, Tetrahedron Lett., 51, 6022 (2010); https://doi.org/10.1016/j.tetlet.2010.09.054
S.K. Sharma, Adv. Org. Chem. Lett., 4, 1 (2017).
F. Diederich, P.J. Stang and R.R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim (2005).
A.L.K. Shi Shun and R.R. Tykwinski, Angew. Chem. Int. Ed., 45, 1034 (2006); https://doi.org/10.1002/anie.200502071
F. Bohlmano, T. Burkhardt and C. Zdero, Naturally Occurring Acetylenes; Academic Press: London (1973).
S.F. Mayer, A.R. Steinreiber, V.A. Orru and K.J. Faber, Org. Chem., 67, 9115 (2002); https://doi.org/10.1021/jo020073w
G. Zeni, R.B. Panatieri, E. Lissner, P.H. Menezes, A.L. Braga and H.A. Stefani, Org. Lett., 3, 819 (2001); https://doi.org/10.1021/ol006946v
M. Ladika, T.E. Fisk, W.W. Wu and S.D. Jons, J. Am. Chem. Soc., 116, 12093 (1994); https://doi.org/10.1021/ja00105a076
A. Stütz, Angew. Chem. Int. Ed. Engl., 26, 320 (1987); https://doi.org/10.1002/anie.198703201
S. Gupta, P.K. Agarwal, M. Saifuddin and B. Kundu, Tetrahedron Lett., 52, 5752 (2011); https://doi.org/10.1016/j.tetlet.2011.08.079
H. Jiang, W. Zeng, Y. Li, W. Wu, L. Huang and W. Fu, J. Org. Chem., 77, 5179 (2012); https://doi.org/10.1021/jo300692d
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S. Kramer, J.L.H. Madsen, M. Rottländer and T. Skrydstrup, Org. Lett., 12, 2758 (2010); https://doi.org/10.1021/ol1008685
V. Gevorgyan, A. Takeda and Y. Yamamoto, J. Am. Chem. Soc., 119, 11313 (1997); https://doi.org/10.1021/ja971935r
H. Sun, X. Wu and R. Hua, Tetrahedron Lett., 52, 4408 (2011); https://doi.org/10.1016/j.tetlet.2011.06.046
R. Singha, S. Nandi and J.K. Ray, Tetrahedron Lett., 53, 6531 (2012); https://doi.org/10.1016/j.tetlet.2012.09.079
Y.-H. Wang, H. Liu, L.-L. Zhu, X.-X. Li and Z. Chen, Adv. Synth. Catal., 353, 707 (2011); https://doi.org/10.1002/adsc.201000833
L. Wang, X. Yu, X. Feng and M. Bao, J. Org. Chem., 78, 1693 (2013); https://doi.org/10.1021/jo302732v
V. Fiandanese, D. Bottalico, G. Marchese, A. Punzi and F. Capuzzolo, Tetrahedron, 65, 10573 (2009); https://doi.org/10.1016/j.tet.2009.10.078
A.K. Mandadapu, S.K. Sharma, S. Gupta, D.G.V. Krishna and B. Kundu, Org. Lett., 13, 3162 (2011); https://doi.org/10.1021/ol201092k
A.K. Mandadapu, M.D. Dathi, R.K. Arigela and B. Kundu, Tetrahedron, 68, 8207 (2012); https://doi.org/10.1016/j.tet.2012.07.067
Q. Zheng, R. Hua, J. Jiang and L. Zhang, Tetrahedron, 70, 8252 (2014); https://doi.org/10.1016/j.tet.2014.09.025
M. Itoh, M. Shimizu, K. Hirano, T. Satoh and M. Miura, J. Org. Chem., 78, 11427 (2013); https://doi.org/10.1021/jo401992d
D. Alves, C. Luchese, C.W. Nogueira and G. Zeni, J. Org. Chem., 72, 6726 (2007); https://doi.org/10.1021/jo070835t
J. Tang and X. Zhao, RSC Adv., 2, 5488 (2012); https://doi.org/10.1039/c2ra20326j
Y. Nishihara, M. Okamoto, Y. Inoue, M. Miyazaki, M. Miyasaka and K. Takagi, Tetrahedron Lett., 46, 8661 (2005); https://doi.org/10.1016/j.tetlet.2005.10.056
Y. Nishihara, K. Ikegashira, K. Hirabayashi, J. Ando, A. Mori and T. Hiyama, J. Org. Chem., 65, 1780 (2000); https://doi.org/10.1021/jo991686k
Z. Chen, H. Jiang, A. Wang and S. Yang, J. Org. Chem., 75, 6700 (2010); https://doi.org/10.1021/jo101216m
S. Xue, L.-G. Meng and Q.-X. Guo, Synth. Commun., 38, 2243 (2008); https://doi.org/10.1080/00397910802026568
S.V. Damle, D. Seomoon and P.H. Lee, J. Org. Chem., 68, 7085 (2003); https://doi.org/10.1021/jo034727s
M.S. Maji, T. Pfeifer and A. Studer, Angew. Chem. Int. Ed., 47, 9547 (2008); https://doi.org/10.1002/anie.200804197
M.W. Paixão, M. Weber, A.L. Braga, J.B. de Azeredo, A.M. Deobald and H.A. Stefani, Tetrahedron Lett., 49, 2366 (2008); https://doi.org/10.1016/j.tetlet.2008.02.083
K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 16, 4467 (1975); https://doi.org/10.1016/S0040-4039(00)91094-3
E. Valenti, M.A. Pericàs and F. Serratosa, J. Am. Chem. Soc., 112, 7405 (1990); https://doi.org/10.1021/ja00176a056
P. Cadiot and W. Chodkiewicz, Eds.: H.G. Viehe, In Chemistry of Acetylenes, Marcel Dekker: New York, pp 597 (1969).
G. Engliton and A.R. Galbraith, Chem. Ind., 737 (1956).
Q. Sun, Z. Lv, Y. Du, Q. Wu, L. Wang, L. Zhu, X. Meng, W. Chen and F.-S. Xiao, Chem. Asian J., 8, 2822 (2013); https://doi.org/10.1002/asia.201300690
A.S. Hay, J. Org. Chem., 27, 3320 (1962); https://doi.org/10.1021/jo01056a511
D. Wang, J. Li, N. Li, T. Gao, S. Hou and B. Chen, Green Chem., 12, 45 (2010); https://doi.org/10.1039/B917448F
K. Yin, C. Li, J. Li and X. Jia, Green Chem., 13, 591 (2011); https://doi.org/10.1039/c0gc00413h
L. Bettanin, G.V. Botteselle, M. Godoi and A.L. Braga, Green Chem. Lett. Rev., 7, 105 (2014); https://doi.org/10.1080/17518253.2014.895868
D. Wang, J. Li, N. Li, T. Gao, S. Hou and B. Chen, Green Chem., 12, 45 (2010); https://doi.org/10.1039/B917448F