C-H Allylation and [3 + 2] Dipolar Cycloaddition between Azomethine Imines and Vinyl Cyclopropanes under Rh(III)
Chaeeun Kim1, Anand Kumar1, Ju Young Kang1
1School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
Abstract:
A rhodium(III)-catalyzed C-H functionalization of azomethine imines with vinyl cyclopropanes (VCPs) is proposed. Mechanistically, VCPs participate in olefin insertion and β-C elimination to produce allylated intermediates, which undergo endotype [3 + 2] dipolar cycloaddition, providing indenopyrazolopyrazolones. Post-transformations of malonate-containing tetracyclic N-heterocycles highlight the synthetic relevance of the proposed method.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Electrophilic Addition to Alkynes: Hydrohalogenation
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Cycloaddition Reactions: Overview
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.


