(E)-1,2-Difluoro-1-iodo-2-trialkylsilanes—A useful synthon for the addition of the [IFC CF] unit to activated electrophiles |
| |
Authors: | Ya-Bo He Ba V Nguyen Donald J Burton |
| |
Institution: | Department of Chemistry, The University of Iowa, Iowa City, IA 52242, USA |
| |
Abstract: | Fluoride ion catalyzed reaction of (E)-IFC CFSiR3 with activated aromatic aldehydes and ketones and activated perfluoroaromatics, such as pentafluoropyridine and perfluorotoluenes, transfers the IFC CF] unit to the activated electrophiles to stereospecifically provide (E)-1,2-difluoro-1-iodosubstituted derivatives. Aluminum chloride catalyzed reaction of (E)-1,2-difluoro-1-iodo-2-trialkylsilanes with alkyl or aryl acyl halides gives the corresponding (E)-1,2-difluoro-1-iodoketones stereospecifically in excellent yield. The vinyl iodide product formed via this methodology could be coupled (with Pd(0)) catalysis to provide an entry to a polyfunctionalized derivative. |
| |
Keywords: | Fluorinated vinylsilanes Fluoride ion mediated reactions [IFC length as m-dash" alt="double bond length as m-dash" src="http://www sciencedirect com/scidirimg/entities/dbnd" style="vertical-align:middle CF] addition reactions" target="_blank">">CF] addition reactions Perfluoroaromatics AlCl3 catalysis |
本文献已被 ScienceDirect 等数据库收录! |