88304-20-5Relevant articles and documents
A BEt3-Base Catalyst for Amide Reduction with Silane
Yao, Wubing,Fang, Huaquan,He, Qiaoxing,Peng, Dongjie,Liu, Guixia,Huang, Zheng
supporting information, p. 6084 - 6093 (2019/05/24)
Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.
Aminomethylation reaction of Ortho -pyridyl C-H bonds catalyzed by group 3 metal triamido complexes
Nagae, Haruki,Shibata, Yu,Tsurugi, Hayato,Mashima, Kazushi
supporting information, p. 640 - 643 (2015/01/30)
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.
Convenient synthesis of angular triquinane from 4-alkenylfulvene via thermal cycloaddition followed by skeletal rearrangement of the resulting [4 + 2] adduct
Inagaki, Sho,Imura, Keisuke,Morita, Toshio,Yoshimi, Yasuharu,Hatanaka, Minoru,Kawano, Tomikazu
, p. 454 - 455 (2008/09/20)
Alkenylfulvene prepared by the annulation of allylidenetriphenylphosphorane with 1,4-ynedione proceeded thermal cyclo-addition in a highly regio- and stereoselective manner to give [4 + 2] adduct which was then converted into triquinane derivative by the