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C(sp₃)-H bond activation with triel metals: indium and gallium zwitterions through internal hydride abstraction in rigid salan ligands.

Abstract : The hydropyrimidine salan (salan=N,N'-dimethyl-N,N'-bis[(2-hydroxyphenyl)methylene]-1,2-diaminoethane) proteo-ligands with a rigid backbone {ON^(CH2)^NO}H2 react with M(CH2SiMe3)3 (M=Ga, In) to yield the zwitterions {ON^(CH(+))^NO}M(-)(CH2SiMe3)2 (M=Ga, 2; In, 3) by abstraction of a hydride from the ligand backbone followed by elimination of dihydrogen. By contrast, with Al2Me6, the neutral-at-metal bimetallic complex [{ON^(CH2)^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(sp3)-H bond activation follows the order Al≪Ga
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01114342
Contributor : Laurent Jonchère <>
Submitted on : Monday, February 9, 2015 - 11:42:37 AM
Last modification on : Thursday, March 5, 2020 - 2:06:35 PM

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Nicolas Maudoux, Jian Fang, Thierry Roisnel, Vincent Dorcet, Laurent Maron, et al.. C(sp₃)-H bond activation with triel metals: indium and gallium zwitterions through internal hydride abstraction in rigid salan ligands.. Chemistry - A European Journal, Wiley-VCH Verlag, 2014, 20 (25), pp.7706-17. ⟨10.1002/chem.201402358⟩. ⟨hal-01114342⟩

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