Functionalization of pyridyl ketones using deprotolithiation-in situ zincation

Madani Hedidi (1, 2) , William Erb (1) , Frédéric Lassagne (1) , Yury S. Halauko (3) , Oleg A. Ivashkevich (3) , Vadim E. Matulis (3) , Thierry Roisnel (1) , Ghenia Bentabed-Ababsa (2) , Florence Mongin (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LSOA - Laboratoire de Synthèse Organique Appliquée [Oran]
3 Belarusian State University

The metallation of aryl ketones was achieved by using LiTMP in the presence of ZnCl2 center dot TMEDA, as evidenced by subsequent interception with iodine or by a palladium-catalysed cross-coupling reaction. One of the synthesized iodo ketones has been further elaborated to reach derivatives of biological interest.

Keywords: ch acidity relationships; carbon bond formation; center-dot-licl; deprotonative metalation; polysubstituted aromatics; directed lithiation; coupling reactions; pyridines; regioselectivity; heteroarenes

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

Madani Hedidi, William Erb, Frédéric Lassagne, Yury S. Halauko, Oleg A. Ivashkevich, et al.. Functionalization of pyridyl ketones using deprotolithiation-in situ zincation. RSC Advances, 2016, 6 (68), pp.63185--63189. ⟨10.1039/c6ra11370b⟩. ⟨hal-01357392⟩