Sonogashira Cross‐Coupling Reaction of Bromocyanofluoro Pyridine Compounds: Access to 5‐ and 6‐Alkynylfluoropyridinamidoximes Scaffolds. Issue 30 (16th August 2021)

• Record Type: Journal Article
• Authors: Razafindrainibe, Franck; Voros, Camille; Jagadeesh, Yerri; Reddy, Nimmakayala Mallikarjuna; Tissier, Allan; Mardy, Keven; Reihanian‐Hadany, Norbert; Brown, Richard C. D.; Baati, Rachid
• Is Part Of: European journal of organic chemistry. Issue 30(2021)
• Page Start: 4393
• Page End: 4397
• Publication Date: 2021-08-16
• Subjects: 15N labeled amidoxime -- Alkynyl-fluoropyridinamidoxime -- Fluorocyanopyridine -- Sonogashira cross-coupling -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100563
• Languages: English
• ISSNs: 1434-193X

Abstract

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‐substituted alkynes and strained saturated heterocycles. Abstract : A novel and operationally simple two‐step protocol, to access highly valuable and underexplored alkynyl‐fluoro‐pyridinamidoximes compounds is reported. These highly functionalized relevant scaffolds may find numerous applications in heterocyclic and medicinal chemistry.