Regioselectivity-Switchable Catalytic Annulations of Alkynyl α-Diketones and α-Cyanoketones

Abstract

Regioselectivity-switchable reactions hold irreplaceable importance in the construction of diversified architectures. In this work, Brønsted base-catalyzed regioselectivity-switchable annulations between alkynyl α-diketones and α-cyanoketones have been achieved for the first time, delivering a series of skeletally thoroughly different dihydrofurofuran and furan derivatives. A range of novel transformations of the products can be realized. The work also demonstrates the unique features of alkynyl α-diketone chemistry, which are in sharp contrast to the current understanding of ynone-related chemistry.

A Review on the Synthesis and Applications of α‐Alkylidene Succinimides

“…Synthesis of diversified molecules through switchable chemoselective and chemo-divergent reaction with the same set of starting materials by simple altering reaction conditions is one of the alluring approaches in organic synthesis. [33,34] In this context, Jiang and co-workers demonstrated an elegant strategy for the synthesis of N-heterocyclic compounds with moderate to excellent yields by tuning reaction conditions from same set of the starting materials.…”

Theoretical Investigation on the Mechanism and Selectivity of Catalyst-Free Annulation of Ynediones and (Iso)quinoline N-Oxides

“…The work demonstrates unique features of alkynyl α-diketone in sharp contrast to that of ynone-related chemistry. 17 Chen has obtained hydroxy spirocyclopenteneindenedione with strong crystallization-induced emission and data storage application via cascade annulation between alkynyl 1,2-diketones and indene-1,3-diones. 18 However, these reactions usually need catalyst or additive or high temperature.…”