139218-72-7Relevant academic research and scientific papers
S(RN)1 reactions of chlorotrifluoromethyl pyridines with naphtholate, phenolate and malonate anions
Beugelmans,Chastanet
, p. 7883 - 7890 (1993)
2-Chloropyridines, bearing a CF3 group on position 3, 4, 5 or 6 (2-Cl Py CF3) were found to be suitable substrates for photostimulated S(RN)1 reactions with nucleophiles derived from 2-naphthol (Nap-OH) or from phenol (PhOH). Carbon-carbon coupling between the regiospecifically generated 2-pyridyl radical and the carbanionic site of the nucleophile yields 2-heterobiaryl derivatives (CF3Py-Nap-OH or CF3Py-PyOH). Similarly, coupling of the 2-amino-5-CF3-pyridyl) radical yields 3-heterobiaryl derivatives. Coupling of the malonate anion takes place with the aforementioned radicals.
Electrosynthesis of Unsymmetrical Polyaryls by a SRN1-Type Reaction
Boy, P.,Combellas, C.,Suba, C.,Thiebault, A.
, p. 4482 - 4489 (2007/10/02)
Unsymmetrical polyaryls are electrosynthesized in liquid ammonia by a single-step SRN1 reaction in the presence of a redox mediator starting from aromatic halides and 2,6-di-tert-butyl phenoxide.With monoaryl halides activated by electron-withdrawing substituents (N of pyridyl or quinolyl, trifluoromethyl, cyano, sulfone, ester, ketone, alkyl sulfide, N(1+) of anilinium), biaryls are obtained in good yields (between 50 and 95percent).The yields of ter- and quateraryls are lower (40percent maximum).The reaction is extended to other ortho-disubstituted phenols.Elimination reactions of the tert-butyl groups from the products are achieved by a Friedel-Crafts reaction using either trifluoromethanesulfonic acid or aluminum trichloride as catalysts.
