A Simple and Efficient Synthesis of Functionalized Cyclic Carbonate Monomers Using a Versatile Pentafluorophenyl Ester Intermediate
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- 作者：Daniel P. Sanders ; Kazuki Fukushima ; Daniel J. Coady ; Alshakim Nelson ; Masaki Fujiwara ; Manabu Yasumoto ; James L. Hedrick
- 刊名：Journal of the American Chemical Society
- 出版年：2010
- 出版时间：October 27, 2010
- 年：2010
- 卷：132
- 期：42
- 页码：14724-14726
- 全文大小：153K
- 年卷期：v.132,no.42(October 27, 2010)
- ISSN：1520-5126
文摘
An improved two-step synthetic route to functionalized cyclic carbonate monomers that features a novel cyclic carbonate intermediate with an active pentafluorophenyl ester group (MTC-OPhF5) has been developed. The versatile pentafluorophenyl ester intermediate can be synthesized on the gram to kilogram scale in one high-yielding step and is easy to store and handle on the benchtop. The active pentafluorophenyl ester of MTC-OPhF5 is amenable to further substitution with suitable nucleophiles such as alcohols and amines to generate functionalized cyclic carbonates in high yields. The substitution reaction is tolerant of a wide variety of functionalities, including various hydrophobic and hydrophilic groups, reactive functionalities (via thiol−ene click chemistry or alkyl halides), and protected acids, alcohols, thiols, and amines. In view of the ever-increasing need for biodegradable and biocompatible polymers, this new methodology provides a simple and versatile platform for the synthesis of new and innovative materials.