Journal
JOURNAL OF MOLECULAR LIQUIDS
Volume 325, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.molliq.2020.115174
Keywords
Cross-coupling reaction; Hiyama; Regioselective; Suzuki-Miyaura
Funding
- Bu-Ali Sina University Research Councils
- Iran National Science Foundation (INSF) [97010990]
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This research aims to establish a more suitable reaction pathway and cross-coupling mechanism for the formation of certain derivatives of quinoxaline and benzofuran by comparing the mechanisms of Suzuki-Miyaura and Hiyama cross-coupling reactions. The findings suggest that the Pd-NHC type complex approach is more desirable for the development of regioselective compounds in competition between different types of cross-coupling reactions.
Pd-NHC type complexes are supposed to have a high degree of participation in 'C-C' cross-coupling reactions, so they are commonly used in industry as well as academia. As regards the competition between Hiyama and Suzuki-Miyaura, this research aims to establish amore suitable reaction pathway and cross-coupling mechanism for the formation of certain derivatives of quinoxaline and benzofuran at the Cam-B3LYP-D3 theoretical level. First of all, the 2-phenyl-toluene formation cycle was determined using two specified cross-coupling reactions due to the presence of experimental 2-phenyl-toluene formation data in both Suzuki-Miyaura and Hiyama cross-coupling reactions. The mechanisms for the development of regioselective compounds 2-(2-methoxyphenyl)-6-p-tolylquinoxaline and 2,3-bis (4-chlorophenyle) benzofuran by Suzuki-Miyaura and Hiyama cross-coupling reactions are computationally compared to more suitable reaction pathways and cross-coupling reactions. In particular, our findings are consistent with the Pd-NHC type complex approach to this problem, which is more desirable for the development of regioselective compounds in competition between the various types of cross-coupling reaction mechanisms. (C) 2020 Elsevier B.V. All rights reserved.
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