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

Rabah Azzouz; Laurent Bischoff; Corinne Fruit; Francis Marsais

doi:10.1055/s-2006-947340

Journal articles

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

Document type :

Journal articles

Domain :

Chemical Sciences

Chemical Sciences / Organic chemistry

Chemical Sciences / Medicinal Chemistry

Chemical Sciences / Radiochemistry

Chemical Sciences / Material chemistry

Chemical Sciences / Inorganic chemistry

Chemical Sciences / Catalysis

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https://hal-normandie-univ.archives-ouvertes.fr/hal-02385070
Contributor : Laurent Bischoff Connect in order to contact the contributor
Submitted on : Thursday, November 28, 2019 - 4:12:44 PM
Last modification on : Wednesday, December 1, 2021 - 2:42:21 PM

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

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

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