Premium
Diethylsilane as a Powerful Reagent in Au Nanoparticle‐Catalyzed Reductive Transformations
Author(s) -
Louka Anastasia,
Kidonakis Marios,
Saridakis Iakovos,
ZantiotiChatzouda ElisavetMaria,
Stratakis Manolis
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000483
Subject(s) - reductive amination , chemistry , catalysis , reagent , aldehyde , amine gas treating , combinatorial chemistry , reactivity (psychology) , reducing agent , solvent , nanoparticle , reductive elimination , organic chemistry , nanotechnology , materials science , medicine , alternative medicine , pathology
Diethylsilane (Et 2 SiH 2 ), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol‐%) supported on TiO 2 . It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N ‐arylisoindolines is also shown in the reductive amination between o ‐phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N ,2‐diphenylisoindolin‐1‐imines are reduced stepwise to the isoindolines. Finally, Et 2 SiH 2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au (0) ‐catalyzed protocols.