Application of Tertiary Amines Synthesized by Catalytic Dehydrogenation of Enamines as Nucleophilic C-2 Synthons for 1,4-Conjugate Addition with Fluoroalkylated Olefins

作者：Morigaki Atsunori; Kawamura Mio; Arimitsu Satoru; Ishihara Takashi; Konno Tsutomu^*

来源：Asian Journal of Organic Chemistry, 2013, 2(3): 239-243.

DOI：10.1002/ajoc.201300007

• amines
• 1,4-conjugate addition
• dehydrogenation
• enamines
• olefins

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.

• 出版日期2013-3