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