Calix[4]pyrroles as macrocyclic organocatalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide

Maeda Chihiro; Sasaki Sota; Takaishi KazutoEma Tadashi

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Calix[4]pyrroles as macrocyclic organocatalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide

机译：杯[4]吡咯与大环的organocatalysts合成的环碳酸盐环氧化合物和二氧化碳

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摘要

Calix[4]pyrrole 1, calix[4]arene 2, or porphyrin 3 together with tetrabutylammonium iodide (TBAI) catalyzed the conversion of epoxides and CO2 into 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.

机译：杯[4]吡咯1杯[4]芳烃2,或卟啉3一起四丁铵碘(TBAI)催化环氧化合物和二氧化碳的转换循环碳酸盐。meso-octamethylcalix[4]吡咯1,合成容易的一步催化缩合为吡咯丙酮,被发现是一个非常活跃和鲁棒性organocatalyst。1采用一个1,3-alternate构象稳定期间生成的阴离子物种催化。环氧开环步,一个pyrrolic NH组和四丁铵阳离子激活(稍后通知)环氧的氢键而另一个北半球组对边指导I -阴离子,位于远离稍后通知阳离子,对吗在环氧背后攻击。

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《Catalysis science & technology》 |2018年第16期|4193-4198|共6页
作者
Maeda Chihiro; Sasaki Sota; Takaishi KazutoEma Tadashi;
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作者单位

Okayama Univ, Grad Sch Nat Sci & Technol, Div Appl Chem, Okayama 7008530, Japan;

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原文格式 PDF
正文语种英语
中图分类汉语教学;
关键词
Carbonates; Pyrroles; hydrogen bondsCarbon DioxideEpoxy CompoundstetrabutylammoniumsynthesisCations;

机译：碳酸盐;吡咯;氢bondsCarbonDioxideEpoxyCompoundstetrabutylammoniumsynthesisCations;

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1. Synthesis of cyclic carbonates from epoxides or olefins and C02 catalyzed by metal-organic frameworks and quaternary ammonium salts [J] . Olga V. Zalomaeva, Nataliya V. Maksimchu~, Andrey M. Chibiryaev, 能源化学：英文版 . 2013,第001期
2. Synthesis of Cyclic Carbonates from CO2 and Epoxides Catalyzed by Hexaalkylguanidinium Halides [J] . DUAN Hai-feng, LI Sheng-hai, LIN Ying-jie, 高等学校化学研究（英文版） . 2004,第005期
3. Direct synthesis of propylene carbonate from propylene and carbon dioxide catalyzed by quaternary ammonium heteropolyphosphatotungstate–TBAB system [J] . Gongda Zhao, Yi Zhang, Hengyun Zhang, 能源化学：英文版 . 2015,第003期
4. Critical temperatures and pressures of reacting mixture in synthesis of dimethyl carbonate with methanol and carbon dioxide [J] . Xing Cui Guo, Zhang Feng Qin, Guo Fu Wang, 中国化学快报（英文版） . 2008,第002期
5. Synthesis of Dimethyl Carbonate from Methanol and Carbon Dioxide Catalyzed by Potassium Hydroxide under Mild Conditions [J] . 中国化学快报（英文版） . 2005,第009期
6. Carbon dioxide injection in carbonate reservoirs 鈥?a review of CO 22 鈥恮ater鈥恟ock interaction studies [J] . Greenhouse Gases. Science and Technology . 2017,第5期

机译：Carbon dioxide injection in carbonate reservoirs 鈥?a review of CO 22 鈥恮ater鈥恟ock interaction studies
7. Lignin-Based Green Catalyst for the Chemical Fixation of Carbon Dioxide with Epoxides To Form Cyclic Carbonates under Solvent-Free Conditions [O] . Wu Zhilian, Xie Haibo, Yu Xue, 2013

机译：Lignin-Based Green Catalyst for the Chemical Fixation of Carbon Dioxide with Epoxides To Form Cyclic Carbonates under solvent-Free Conditions

Calix[4]pyrroles as macrocyclic organocatalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide

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