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Thermal [2+2]-Cycloaddition between Silyl Alkynes and Allenyl Phenols Followed by the Nucleophilic Addition of Water: Metal-Free and Economical Synthesis of Arylcyclobutenals

Abstract

Herein, we report an unprecedented thermal [2+2]-cycloaddition between silylalkynes and allenylphenols to form the aromatizing cyclobutachromene intermediate, followed by the nucleophilic addition of water to yield functionalized arylcyclobutenals. This reaction is atom- and pot-economical because all atoms contained in the starting material were retained in the final product, no other reactants are required, and it proceeds in one-pot.

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Article information


Submitted
07 Dec 2019
Accepted
09 Jan 2020
First published
13 Jan 2020

Green Chem., 2020, Accepted Manuscript
Article type
Paper

Thermal [2+2]-Cycloaddition between Silyl Alkynes and Allenyl Phenols Followed by the Nucleophilic Addition of Water: Metal-Free and Economical Synthesis of Arylcyclobutenals

S. OHNO, R. F. Avena, H. Aoyama, H. Fujioka and M. Arisawa, Green Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9GC04184B

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