Litcius/Paper detail

Rh-Catalyzed [3+2] Annulation of Cyclic Ketimines and Alkynyl Chloride: A Strategy for Accessing Unsymmetrically Substituted and Highly Functionalizable Indenes

Xu Zhao, Chenrui Fan, Jianbo He, Yunfei Luo

2022Organic Letters24 citationsDOIOpen Access PDF

Abstract

Alkynyl chlorides were found to be extraordinarily novel electrophiles, which could afford a single regioisomer of the [3+2] annulation adducts with cyclic ketimines by rhodium catalysis. The alkenyl chloride moiety in the products provided a valuable functional handle for further diverse transformations. Therefore, this research provided not only a synthetic protocol for accessing unsymmetrically substituted indenyl amines but also a highly divergent solution for decorating the substituting group by postmanipulation of the chloride.

Topics & Concepts

AnnulationChemistryMoietyElectrophileCatalysisAdductChlorideRhodiumStructural isomerCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms