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O -Tetrahydropyran-2-yloxy ( O -THP) as an ortho -Directing Group in the Lithiation of Pyridines

Rabah Azzouz 1 Laurent Bischoff 1 Corinne Fruit 1 Francis Marsais 2
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 IRCOF - Institut de Chimie Organique Fine
Abstract : Herein we report regioselective deprotonations of 3- and 4-(tetrahydropyran-2-yloxy)pyridine with n-butyllithium. Trapping the lithiated species with various electrophiles afforded functionalized pyridines in good yields. A one-pot procedure also allowed the double functionalization at C4 and C2 in the case of 3-O-THP-pyridine. The ortho-metallating ability of this group was examined in comparison with other well-known oxygen-based ortho-directing groups.
Keywords : acetals pyridines metallations lithium organometallic reagents
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Journal articles
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02385070
Contributor : Laurent Bischoff <>
Submitted on : Thursday, November 28, 2019 - 4:12:44 PM
Last modification on : Thursday, July 2, 2020 - 3:29:13 AM

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COMUE-NORMANDIE | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | CNRS | ENSICAEN | UNILEHAVRE | UNICAEN

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Rabah Azzouz, Laurent Bischoff, Corinne Fruit, Francis Marsais. O -Tetrahydropyran-2-yloxy ( O -THP) as an ortho -Directing Group in the Lithiation of Pyridines. SYNLETT, Georg Thieme Verlag, 2006, 2006 (12), pp.1908-1912. ⟨10.1055/s-2006-947340⟩. ⟨hal-02385070⟩

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