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Application of Tertiary Amines Synthesized by Catalytic Dehydrogenation of Enamines as Nucleophilic C 2 Synthons for 1,4‐Conjugate Addition with Fluoroalkylated Olefins
Author(s) -
Morigaki Atsunori,
Kawamura Mio,
Arimitsu Satoru,
Ishihara Takashi,
Konno Tsutomu
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300007
Subject(s) - chemistry , synthon , dehydrogenation , catalysis , nucleophile , conjugate , organic chemistry , tertiary amine , nucleophilic addition , tertiary alcohols , combinatorial chemistry , medicinal chemistry , mathematical analysis , mathematics
A catalytic amount of Pd(OAc) 2 was successfully applied for the generation of enamines from various tertiary amines under oxidative conditions. As a synthetic application, the generated enamines were used for 1,4‐conjugate addition reactions with fluoroalkylated olefins. Thus, a catalytic amount of Pd(OAc) 2 was added to a mixture of tertiary amines and fluoroalkylated olefins in N , N ,‐dimethylacetamide in air, and the corresponding 1,4‐adducts were obtained in moderate to good yields for a variety of substrates. This unique reaction can allow readily available tertiary amines to be used as nucleophilic C2 synthons and is an alternative synthetic protocol for the hydroformylmethylation of olefins.