Functionalization of pyridyl ketones using deprotolithiation-in situ zincation

Madani Hedidi; William Erb; Frédéric Lassagne; Yury S. Halauko; Oleg A. Ivashkevich; Vadim E. Matulis; Thierry Roisnel; Ghenia Bentabed-Ababsa; Florence Mongin

doi:10.1039/c6ra11370b

Journal articles

Functionalization of pyridyl ketones using deprotolithiation-in situ zincation

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

1 ISCR - Institut des Sciences Chimiques de Rennes

2 Laboratoire de Synthèse Organique Appliquée

Abstract : 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

Document type :

Journal articles

Domain :

Chemical Sciences

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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01357392
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Submitted on : Monday, August 29, 2016 - 4:40:43 PM
Last modification on : Thursday, March 5, 2020 - 2:03:16 PM

Functionalization of pyridyl ketones using deprotolithiation-in situ zincation

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Functionalization of pyridyl ketones using deprotolithiation-in situ zincation

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