Tris[N,N-bis(trimethylsilyl)amido] complexes of group 3 metals, esp. yttrium and gadolinium, served as catalysts for ortho-C-H bond addn. of pyridine derivs. and N-heteroaroms. into the C=N double bond of nonactivated imines to afford the corresponding aminomethylated products. Addn. of catalytic amts. of secondary amines, such as dibenzylamine, dramatically improved the catalytic activity through the formation of a mixed ligated complex such as [(Me3Si)2N]2Y(NBn2)(THF) (4). Furthermore, kinetic studies using the isolated complex 4 provided a plausible reaction mechanism by which coordination of two pyridine derivs. afforded a penta-coordinated species as a key step. [on SciFinder(R)]
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