Chemoselective Silylative Reduction of Conjugated Nitriles under Metal-Free Catalytic Conditions: β-Silyl Amines and Enamines

Autor:	Juhyeon Park, Sehoon Park, Narasimhulu Gandhamsetty, Jinseong Jeong, Sukbok Chang, Sung-Woo Park
Rok vydání:	2015
Předmět:	Nitrile Silylation Hydrosilylation Enantioselective synthesis General Medicine General Chemistry Conjugated system Catalysis Enamine chemistry.chemical_compound chemistry Organic chemistry Amine gas treating Organic synthesis
Zdroj:	Angewandte Chemie International Edition. 54:6832-6836
ISSN:	1433-7851
DOI:	10.1002/anie.201502366
Popis:	The B(C6F5)3-catalyzed silylative reduction of conjugated nitriles has been developed to afford synthetically valuable β-silyl amines. The reaction is chemoselective and proceeds under mild conditions. Mechanistic elucidation indicates that it proceeds by rapid double hydrosilylation of the conjugated nitrile to an enamine intermediate which is subsequently reduced to the β-silyl amine, thus forming a new C(sp(3))-Si bond. Based on this mechanistic understanding, a preparative route to enamines was also established using bulky silanes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::aa44acfab4936be0c57413df2d2dafda https://doi.org/10.1002/anie.201502366 Zobrazit plný text záznamu Plný text