Fe-catalyzed Decarbonylative Alkylative Spirocyclization of <i>N</i>-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones
Xiang Peng,
Ren-Xiang Liu,
Xiang-Yan Xiao,
Luo Yang
Affiliations
Xiang Peng
Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Hunan 411105, China
Ren-Xiang Liu
Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Hunan 411105, China
Xiang-Yan Xiao
Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Hunan 411105, China
Luo Yang
Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Hunan 411105, China
For the convenient introduction of simple linear/branched alkyl groups into biologically important azaspirocyclohexadienones, a practical Fe-catalyzed decarbonylative cascade spiro-cyclization of N-aryl cinnamamides with aliphatic aldehydes to provide alkylated 1-azaspiro-cyclohexadienones was developed. Aliphatic aldehydes were oxidative decarbonylated into primary, secondary and tertiary alkyl radicals conveniently and allows for the subsequent cascade construction of dual C(sp3)-C(sp3) and C=O bonds via radical addition, spirocyclization and oxidation sequence.
