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Issue 83, 2020
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Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings via C[triple bond, length as m-dash]C bond cleavage

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Abstract

The first synthesis of eight-membered N-containing heterocycles by oxidative bicyclization/ring extension of arylacetylenes and aryl amines has been achieved. This protocol uses arylacetylene as an unusual two-carbon synthon by incorporating the two parts of the cracked C[triple bond, length as m-dash]C bond into the final product, which provides a new method for using arylacetylenes as two-carbon synthons and further enriches C[triple bond, length as m-dash]C bond cleavage methodology. Moreover, this multi-component reaction can provide diverse fused elegant eight-membered N-heterocycles under mild conditions with wide substrate scopes.

Graphical abstract: Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings via C [[triple bond, length as m-dash]] C bond cleavage

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Article information


Submitted
06 Aug 2020
Accepted
07 Sep 2020
First published
07 Sep 2020

Chem. Commun., 2020,56, 12554-12557
Article type
Communication

Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings via C[triple bond, length as m-dash]C bond cleavage

P. Zhao, X. Yu, Y. Zhou, C. Huang, Y. Wu, Y. Zhu and A. Wu, Chem. Commun., 2020, 56, 12554
DOI: 10.1039/D0CC05363E

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