C       sp       3      H Bond Activation with Triel Metals: Indium and Gallium Zwitterions through Internal Hydride Abstraction in Rigid Salan Ligands | Zendy

Maudoux Nicolas | Zendy; Fang Jian | Zendy; Roisnel Thierry | Zendy; Dorcet Vincent | Zendy; Maron Laurent | Zendy; Carpentier JeanFrançois | Zendy; Sarazin Yann | Zendy

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C sp 3 H Bond Activation with Triel Metals: Indium and Gallium Zwitterions through Internal Hydride Abstraction in Rigid Salan Ligands

Author(s) -

Maudoux Nicolas,

Fang Jian,

Roisnel Thierry,

Dorcet Vincent,

Maron Laurent,

Carpentier JeanFrançois,

Sarazin Yann

Publication year - 2014

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201402358

Subject(s) - chemistry , protonolysis , hydride , moiety , zwitterion , ligand (biochemistry) , medicinal chemistry , methylene , steric effects , stereochemistry , metal , crystallography , molecule , organic chemistry , catalysis , biochemistry , receptor

The hydropyrimidine salan (salan= N , N ′‐dimethyl‐ N , N ′‐bis[(2‐hydroxyphenyl)methylene]‐1,2‐diaminoethane) proteo‐ligands with a rigid backbone {ON^(CH 2 )^NO}H 2 react with M(CH 2 SiMe 3 ) 3 (M=Ga, In) to yield the zwitterions {ON^(CH + )^NO}M − (CH 2 SiMe 3 ) 2 (M=Ga, 2 ; In, 3 ) by abstraction of a hydride from the ligand backbone followed by elimination of dihydrogen. By contrast, with Al 2 Me 6 , the neutral‐at‐metal bimetallic complex [{ON^(CH 2 )^NO}AlMe] 2 ( [1] 2 ) is obtained quantitatively. The formation of indium zwitterions is also observed with sterically more encumbered ligands containing o ‐Me substituents on the phenolic rings, or an N (CHPh) N moiety in the heterocyclic core. Overall, the ease of C sp 3H bond activation follows the order Al≪Ga

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