Nickel-Catalyzed Formal [3+2+2] Cycloadditions of Bis(trimethylsilyl)cyclopropanone withDiynes: A Concise Approach to Functionalized Azulene Derivatives
Year: 2026
Type: preprint
Abstract: consequently, developing efficient methods for their preparation is important. Herein, we report the development of formal [3+2+2] cycloaddition chemistry involving 1,6-diynes and cis-2,3-bis(trimethylsilyl)cyclopropanone as a new synthetic approach to functionalized azulene derivatives. The azulene framework is efficiently constructed using the developed reaction, with synthetically versatile functional groups introduced in a single operation. An unusual rearrangement process consistent with a formal [1,7]-silyl migration from the C7 to C6 position of the azulene framework was observed during the course of the transformation. The synthetic utility of the method was demonstrated by further transforming the resulting silylated azulene derivatives into a variety of 1functionalized azulenes. This study provides a new strategy for constructing and functionalizing azulene skeletons as well as new insight into the reactivities of cyclopropanone-derived intermediates.
Source: ChemRxiv
Institution: Meiji Pharmaceutical University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7213916249