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

Jacob S McMullen; Andrew J P White; Mark R Crimmin

doi:10.1039/d3cc04594c

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

Chem Commun (Camb). 2023 Dec 12;59(99):14681-14684. doi: 10.1039/d3cc04594c.

Authors

Jacob S McMullen¹, Andrew J P White¹, Mark R Crimmin¹

Affiliation

¹ Department of Chemistry, Imperial College London, 82 Wood Lane, Shepherds Bush, London, W12 0BZ, UK. [email protected].

PMID: 37997165
DOI: 10.1039/d3cc04594c

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.