Ring-expansion and desulfurisation of thiophenes with an aluminium(i) reagent

Literature Information

Publication Date 2023-11-16
DOI 10.1039/D3CC04594C
Impact Factor 6.222
Authors

Jacob S. McMullen, Andrew J. P. White, Mark R. Crimmin


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Abstract

Reactions of thiophene, 2-methylthiophene, 2-methoxythiophene, 2,3-dimethylthiophene, and benzothiophene with the aluminium(I) complex [{ArNC(Me)2H}Al] (Ar = 2,6-di-isopropylphenyl) are reported. In all cases, carbon–sulfur bond activation and ring-expansion of the heterocycle is observed. For thiophene, we identify a reaction network for desulfurisation that includes an unusual second carbon–sulfur bond activation step.

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