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Aminomethylation Reaction of Ortho-Pyridyl C-H Bonds Catalyzed by Group 3 Metal Triamido Complexes

Aminomethylation Reaction of Ortho-Pyridyl C-H Bonds Catalyzed by Group 3 Metal Triamido Complexes

Haruki Nagae, Yu Shibata, Hayato Tsurugi, Kazushi Mashima

J Am Chem Soc. 2015 Jan 21;137(2):640-3.

PMID: 25543453

Abstract:

Tris[N,N-bis(trimethylsilyl)amido] complexes of group 3 metals, especially yttrium and gadolinium, served as catalysts for ortho-C-H bond addition of pyridine derivatives and N-heteroaromatics into the C═N double bond of nonactivated imines to afford the corresponding aminomethylated products. Addition of catalytic amounts 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 derivatives afforded a penta-coordinated species as a key step.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP41836286	Tris[N,N-bis(trimethylsilyl)amide]yttrium		41836-28-6	Price

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