2018年
Calix[4]pyrroles as macrocyclic organocatalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide
Catalysis Science & Technology
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- ,
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- 巻
- 8
- 号
- 16
- 開始ページ
- 4193
- 終了ページ
- 4198
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1039/C8CY00941D
- 出版者・発行元
- Royal Society of Chemistry ({RSC})
© 2018 The Royal Society of Chemistry. Calix[4]pyrrole 1, calix[4]arene 2, or porphyrin 3 together with tetrabutylammonium iodide (TBAI) catalyzed the conversion of epoxides and CO2into cyclic carbonates. Among them, meso-octamethylcalix[4]pyrrole 1a, which was synthesized easily in one step by the acid-catalyzed condensation of pyrrole with acetone, was found to be a very active and robust organocatalyst. DFT calculations suggested that 1a adopts a 1,3-alternate conformation to stabilize the anionic species generated during the catalysis. In the key transition state of the epoxide ring-opening step, one pyrrolic NH group and the tetrabutylammonium (TBA) cation activate the epoxide by hydrogen bonding while another NH group on the opposite side guides the I-anion, which is located away from the TBA cation, to the backside attack on the epoxide.
- リンク情報
- ID情報
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- DOI : 10.1039/C8CY00941D
- ISSN : 2044-4753
- eISSN : 2044-4761
- ORCIDのPut Code : 46898921
- SCOPUS ID : 85052061881