Biologically active pentafluorosulfanyl containing compounds: Synthesis and characterization

ORGN 156

Dong Sung Lim, dl0041@albany.edu1, G. Sankar Lal, lalgs@airproducts.com2, Kristin E. Minnich, minnicke@apci.com3, and John T. Welch, jwelch@uamail.albany.edu1. (1) Department of Chemistry, University at Albany - SUNY, 1400 Washington Avenue, Albany, NY 12222, (2) Corporate Science and Technology Center, Air Products and Chemicals, Inc, 7201 Hamilton Boulevard, Allentown, PA 18195-1501, (3) Corporate Science & Technology Center, Air Products and Chemicals, Inc, 7201 Hamilton Boulevard, Allentown, PA 18195-1501
The pentafluorosulfanyl group has rarely been explored as a substituent in medicinal or pharmaceutical chemistry. Conceptually an analog of the trifluoromethyl group, the pentafluorosulfanyl group presents an octahedral steric demand while retaining the relative stability of the trifluoromethyl group. The preparation of analogs of biologically active trifluoromethylated compounds requires the ready availability of pentafluorosulfanyl containing reagents and building blocks, materials which only recently have become readily available. We have prepared analogs of the herbicide treflan (1), the antidepressant fluoxetine (2), and the anorectic fenfluramine (3) from pentafluorosulfanyl arenes. In addition we also have explored the reactivity those building blocks in electrophilic substitution reactions and in the formation of organometallic reactions while considering the overall stability of this unusual substituent to routine synthetic transformations. We will report our latest results on new approaches to introduce the pentafluorosulfanyl group into non-aromatic compounds with potential biological utility.