88951-00-2Relevant articles and documents
Photoredox-Catalyzed C-F Bond Allylation of Perfluoroalkylarenes at the Benzylic Position
Sugihara, Naoki,Suzuki, Kensuke,Nishimoto, Yoshihiro,Yasuda, Makoto
supporting information, p. 9308 - 9313 (2021/06/28)
Site-selective and direct C-F bond transformation of perfluoroalkylarenes was achieved with allylic stannanes via an iridium photoredox catalyst system. The present defluoroallylation proceeds exclusively at the benzylic position through perfluoroalkyl radicals generated by a single-electron transfer from an excited photoredox catalyst to perfluoroalkylarenes. A variety of perfluoroalkyl groups are applicable: linear perfluoroalkyl-substituted arenes such as Ar-nC4F9and Ar-nC6F13and heptafluoroisopropylarenes (Ar-CF(CF3)2) underwent site-selective defluoroallylation. DFT calculation studies revealed that thein situgenerated Bu3SnF traps F-to prevent a retroreaction from the unstable perfluoroalkyl radical intermediate, and the radical intermediate favorably reacts with allylic stannanes. The synthesis of a bis(trifluoromethyl)methylene unit containing compound, which is an analog that is useful as a pharmaceutical agent for the prophylaxis or treatment of diabetes and inflammatory diseases, demonstrated the utility of this reaction.
A class of effective decarboxylative perfluoroalkylating reagents: [(phen)2Cu](O2CRF)
Huang, Yangjie,Ajitha, Manjaly J.,Huang, Kuo-Wei,Zhang, Zhongxing,Weng, Zhiqiang
supporting information, p. 8468 - 8474 (2016/06/01)
This article describes the invention of a class of effective reagents [(phen)2Cu](O2CRF) (1) for the decarboxylative perfluoroalkylation of aryl and heteroaryl halides. Treatment of copper tert-butyloxide with phenanthroline ligands, with subsequent addition of perfluorocarboxylic acids afforded air-stable copper(i) perfluorocarboxylato complexes 1. These complexes reacted with a variety of aryl and heteroaryl halides to form perfluoroalkyl(hetero)arenes in moderate to high yields. Computational studies suggested that the coordination of the second phen ligand may reduce the energy barrier for the decarboxylation of perfluorocarboxylate to facilitate perfluoroalkylation.
LIQUID CRYSTALS CONTAINING FLUORINE. IX. 4-CYANOPHENYL 4-(PERFLUOROALKYL)BENZOATES AND TRANS-4-(PERFLUOROALKYL)CYCLOHEXANECARBOXYLATES
Fialkov, Yu. A.,Zalesskaya, I. M.,Yagupol'skii, L. M.
, p. 1781 - 1787 (2007/10/02)
By hydrogenation of 4-(perfluoroalkyl)benzoic esters at platinum and subsequent hydrolysis cis- and trans-4-(perfluoroalkyl)cyclohexanecarboxylic acids were obtained.A convenient method was foun for the isolation of the trans isopmers. 4-Phenyl esters of
