Facile synthesis of highly functionalized ethyltrifluoroborates.
Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)2CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA. gmolandr@sas.upenn.edu
Febo-Ayala
Wilma
W
Ortega-Guerra
Montserrat
M
D000478:Alkylation; D001881:Borates / Q000737:chemistry*; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D017680:Potassium Compounds / Q000138:chemical synthesis / Q000737:chemistry
D001881:Borates; D017611:Fluorine Compounds; D005663:Furans; D017680:Potassium Compounds