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Group IV Complexes with Sterically Congested N -Aryl-adamantylcarbamidate Ligands

Name: Group IV Complexes with Sterically Congested N -Aryl-adamantylcarbamidate Ligands
Keywords: Aromatic compounds, Metals, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ligands, Particulate matter, Hydrocarbons

descriptionPublicationkeyboard_double_arrow_right Article 09 Aug 2023 France Publisher:American Chemical Society (ACS)Journal:Organometallics, volume 42, pages 2,304-2,311 (issn: 0276-7333, eissn: 1520-6041,

Authors: Kheirkhah, Bahareh Rezaei; Huadsai, Wimonsiri; Liebing, Phil; Bontemps, Sébastien; Westerhausen, Matthias;

doi: 10.1021/acs.organomet.3c00291

Group IV Complexes with Sterically Congested N -Aryl-adamantylcarbamidate Ligands

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Abstract

[Image: see text] Metalation of N-(2,6-dibenzhydryl-4-tolyl)adamantane-1-carboxamide (1, Ar*N(H)–C(O)–Ad) with M(NMe(2))(4) (M = Ti, Zr, Hf) yields amidate complexes Ar*N=C(Ad)–O–Ti(NMe(2))(3) (2) as well as bis(amidate) compounds (Ar*N=C(Ad)–O)(2)M(NMe(2))(2) (M = Zr (3), Hf (4)). In 2, the amidate ligand acts as a monodentate base via the oxygen atom with the Ti center in a slightly distorted tetrahedral environment. The steric requirement of the amidate ligand stabilizes the small coordination number of four of the Ti atom. In congeners 3 and 4, two bidentate amidate ligands exist in the coordination spheres, leading to hexacoordinate group IV metal atoms. The small bite angles of the Zr- and Hf-bound amidate ligands lead to severe distortion of the octahedral environments of the Zr and Hf centers. Titanium compound 2 is an unsuitable choice to catalyze hydrofunctionalization of alkynes with amines and phosphane oxides and despite the significantly smaller pK(a) value of the carboxylic amide, formation of carboxamide 1 is the dominant reaction upon addition of amines or phosphane oxides to release intramolecular steric strain introduced by the very bulky adamantylamidato ligand.

Country

France

Related Organizations

Institut de Recherche pour le Développement
France
Laboratoire de Chimie de Coordination
France
UNIVERSITE PARIS DESCARTES
France
Friedrich Schiller University Jena
Germany

Keywords

Aromatic compounds, Metals, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ligands, Particulate matter, Hydrocarbons

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CCDC 2220639: Experimental Crystal Structure Determination
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Group IV Complexes with Sterically Congested N -Aryl-adamantylcarbamidate Ligands

Group IV Complexes with Sterically Congested N -Aryl-adamantylcarbamidate Ligands

4 Research products, page 1 of 1

CCDC 2220639: Experimental Crystal Structure Determination

CCDC 2220638: Experimental Crystal Structure Determination

CCDC 2220636: Experimental Crystal Structure Determination

CCDC 2220637: Experimental Crystal Structure Determination