Copyright (c) 2022 AJC
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Catalytic Iodine and Morpholine as Reagent Combination for Hydration of Alkynes via Markovnikov Addition
Corresponding Author(s) : Chandi C. Malakar
Asian Journal of Chemistry,
Vol. 34 No. 6 (2022): Vol 34 Issue 6
Abstract
This work describes the iodine-catalyzed N-methyl morpholine-promoted hydration of alkynes via Markovnikov type addition. The developed protocol provides a direct approach to synthesize methyl ketones under metal-free condition. A series of aromatic alkynes embedded with electron-donating and electron-withdrawing groups were well-investigated to give the corresponding products in good to high yields.
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- A.A. Rajkiewicz, N. Wojciechowska and M. Kalek, ACS Catal., 10, 831 (2020); https://doi.org/10.1021/acscatal.9b04394
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- T. Tsuchimoto, T. Joya, E. Shirakawa and Y. Kawakami, Synlett, 1777 (2000); https://doi.org/10.1055/s-2000-8707
- N. Olivi, E. Thomas, J.-F. Peyrat, M. Alami and J.-D. Brion, Synlett, 2175 (2004); https://doi.org/10.1055/s-2004-831310
- Y. Xu, X. Hu, J. Shao, G. Yang, Y. Wu and Z. Zhang, Green Chem., 17, 532 (2015); https://doi.org/10.1039/C4GC01322K
- M. O’Brien, I. Baxendale and S. Ley, Org. Lett., 12, 1596 (2010); https://doi.org/10.1021/ol100322t
- W. Wang, A. Zheng, P. Zhao, C. Xia and F. Li, ACS Catal., 4, 321 (2014); https://doi.org/10.1021/cs400983y
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References
A.A. Rajkiewicz, N. Wojciechowska and M. Kalek, ACS Catal., 10, 831 (2020); https://doi.org/10.1021/acscatal.9b04394
X. Geng, C. Wang, C. Huang, Y. Bao, P. Zhao, Y. Zhou, Y.-D. Wu, L.- L. Feng and A.-X. Wu, Org. Lett., 22, 140 (2020); https://doi.org/10.1021/acs.orglett.9b04060
F.C. Sousa e Silva, N.T. Van and S.E. Wengryniuk, J. Am. Chem. Soc., 142, 64 (2020); https://doi.org/10.1021/jacs.9b11282
I. Yavari and S. Shaabanzadeh, Org. Lett., 22, 464 (2020); https://doi.org/10.1021/acs.orglett.9b04221
F. Alonso, I.P. Beletskaya and M. Yus, Chem. Rev., 104, 3079 (2004); https://doi.org/10.1021/cr0201068
L. Hintermann and A. Labonne, Synthesis, 1121 (2007); https://doi.org/10.1055/s-2007-966002
H. Kanemitsu, K. Uehara, S. Fukuzumi and S. Ogo, J. Am. Chem. Soc., 130, 17141 (2008); https://doi.org/10.1021/ja807254d
J.A. Goodwin and A. Aponick, Chem. Commun., 51, 8730 (2015); https://doi.org/10.1039/C5CC00120J
X. Liu, L. Liu, Z. Wang and X. Fu, Chem. Commun., 51, 11896 (2015); https://doi.org/10.1039/C5CC04015A
C. Xu, W. Du, Y. Zeng, B. Dai and H. Guo, Org. Lett., 16, 948 (2014); https://doi.org/10.1021/ol403684a
M. Hassam and W.-S. Li, Tetrahedron, 71, 2719 (2015); https://doi.org/10.1016/j.tet.2015.03.034
F. Trentin, A.M. Chapman, A. Scarso, P. Sgarbossa, R.A. Michelin, G. Strukul and D.F. Wass, Adv. Synth. Catal., 354, 1095 (2012); https://doi.org/10.1002/adsc.201100326
J. Park, J. Yeon, P.H. Lee and K. Lee, Tetrahedron Lett., 54, 4414 (2013); https://doi.org/10.1016/j.tetlet.2013.06.015
D. Tyagi, R.K. Rai, S.M. Mobin and S.K. Singh, Asian J. Org. Chem., 6, 1647 (2017); https://doi.org/10.1002/ajoc.201700396
S.B. Ötvös, Z. Szécsényi and F. Fülöp, ACS Sustain. Chem.& Eng., 7, 13286 (2019); https://doi.org/10.1021/acssuschemeng.9b02520
J.-W. Lai, Z.-Y. Liu, X.-Y. Chen, H. Zhang and H.-Y. Liu, Tetrahedron Lett., 61, 152426 (2020); https://doi.org/10.1016/j.tetlet.2020.152426
X. Jin, T. Oishi, K. Yamaguchi and N. Mizuno, Chem. Eur. J., 17, 1261 (2011); https://doi.org/10.1002/chem.201002761
W. Liu, H. Wang and C.-J. Li, Org. Lett., 18, 2184 (2016); https://doi.org/10.1021/acs.orglett.6b00801
T. Tsuchimoto, T. Joya, E. Shirakawa and Y. Kawakami, Synlett, 1777 (2000); https://doi.org/10.1055/s-2000-8707
N. Olivi, E. Thomas, J.-F. Peyrat, M. Alami and J.-D. Brion, Synlett, 2175 (2004); https://doi.org/10.1055/s-2004-831310
Y. Xu, X. Hu, J. Shao, G. Yang, Y. Wu and Z. Zhang, Green Chem., 17, 532 (2015); https://doi.org/10.1039/C4GC01322K
M. O’Brien, I. Baxendale and S. Ley, Org. Lett., 12, 1596 (2010); https://doi.org/10.1021/ol100322t
W. Wang, A. Zheng, P. Zhao, C. Xia and F. Li, ACS Catal., 4, 321 (2014); https://doi.org/10.1021/cs400983y
N. Li, J. Wang, X. Zhang, R. Qiu, X. Wang, J. Chen, S. Yin and X. Xu, Dalton Trans., 43, 11696 (2014); https://doi.org/10.1039/C4DT00549J
B. Liu, F. Jin, T. Wang, X. Yuan and W. Han, Angew. Chem. Int. Ed., 56, 12712 (2017); https://doi.org/10.1002/anie.201707006
S. Devari, A.M. Rizvi and B. Shah, Tetrahedron Lett., 57, 3294 (2016); https://doi.org/10.1016/j.tetlet.2016.06.046