Copper-catalyzed cyanoisopropylation of beta-keto esters using azos: synthesis of beta-dicarbonyls bearing an alfa-tertiary nitrile moiety

Abstract

A copper-catalyzed α-cyanoisopropylation reaction of β-keto esters using azo compounds as cyanoalkylating agents is presented, providing an easy access to β-dicarbonyls containing an α-tertiary nitrile moiety with adjacent tertiary and quaternary carbon centers. It is remarkable because a tremendous steric conflict is involved during reaction. Such nitriles were otherwise unavailable, and the reaction features simple and relatively mild conditions and good functional-group tolerance.

GRAPHICAL ABSTRACT

KEYWORDS:

• Cyanoalkylation
• C-C coupling
• Copper catalysis
• Azo compounds
• β-Dicarbonyls

Additional information

Funding

We gratefully acknowledge the financial support from the National Natural Science Foundation of China [21702083], the General Projects of Yunnan Education Department [2017ZZX093], the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province, and the Yunnan Ten Thousand Talent Program for Young Top-Notch Talents.