DOI: 10.1021/acs.orglett.6c03511 ISSN: 1523-7060
Accelerated Green SN1 Reactions of the 9-Phenyl-9-fluorenyl Group
Kinshuk Ghosh, Kajumee P. Bora Bhowal, Samaneh Zarei, Chloé Ding, Felix Polyak, William D. LubellAbstract
Unimolecular nucleophilic substitution (SN1) reactions are expedited by resonant acoustic mixing (RAM). 9-Phenyl-9-fluorenyl (PhF) halides were rapidly made from PhF-OH by RAM of concentrated toluene/mineral acid mixtures. By RAM of PhF-Br and Et3N in environmentally benign propylene carbonate, N-PhF-amino esters were synthesized from hydrochlorides, including serine and hydroxyproline esters without alcohol side-chain protection. Ester saponification with RAM gave efficiently N-PhF-amino acid. The RAM-assisted SN1 chemistry proved to be proficient for greener PhF installation.