Razafindrainibe, Franck, Voros, Camille, Yerri, Jagadeesh, Nimmakayala Reddy, Mallikarjuna Nimmakayala Reddy, Tissier, Allan, Mardy, Keven, Reihanian-Hadany, Norbert, Brown, Richard C.D. and Baati, Rachid (2021) Sonogashira cross-coupling reaction of bromocyanofluoro pyridine nuclei: access to 5- and 6-alkynylfluoropyridinamidoximes scaffolds. European Journal of Organic Chemistry, 2021 (30), 4393-4397. (doi:10.1002/ejoc.202100563).
Abstract
We disclose a general two-step procedure to access hitherto unknown and under explored 5- and 6-alkynyl-3-fluoro-2-pyridinamidoximes from 5- and 6-bromo-3-fluoro-2-cyanopyridines and a wide range of easily available and bench-stable terminal alkynes, using Sonogashira cross-coupling, as the first step. The generation of the polar amidoxime group is realized at a late-stage upon treatment of the alkynylfluorocyanopyridine by hydroxylamine. This mild and operationally simple two-step room temperature process is compatible with enantiopure chiral substrates and various functionality including free alcohols, unprotected and CBz-protected amines, acetonides, benzyl ethers, amide, imide, di-subsituted alkynes and strained saturated heterocycles.
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