title: A simple and efficient synthesis of functionalized cyclic carbonate monomers using a versatile pentafluorophenyl ester intermediate.
abstract: 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-OPhF(5)) 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-OPhF(5) 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.
authors.affiliation: IBM Almaden Research Center, 650 Harry Road, San Jose, California 95120, United States. dsand@us.ibm.com
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Sanders
authors.forename: Kazuki
authors.initials: K
authors.lastname: Fukushima
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Coady
authors.forename: Alshakim
authors.initials: A
authors.lastname: Nelson
authors.forename: Masaki
authors.initials: M
authors.lastname: Fujiwara
authors.forename: Manabu
authors.initials: M
authors.lastname: Yasumoto
authors.forename: James L
authors.initials: JL
authors.lastname: Hedrick
mesh_terms: D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004952:Esters; D005464:Fluorobenzenes / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D005466:Fluorocarbons
chemical_list: D002254:Carbonates; D004952:Esters; D005464:Fluorobenzenes; D010636:Phenols; C085539:2,3,4,5,6-pentafluorophenol; D005466:Fluorocarbons