Indium‐Catalysed Transfer Hydrogenation for the Reductive Cyclisation of 2‐Alkynyl Enones towards Trisubstituted Furans
Luomo Li, Sascha Kail, Sebastian M. Weber, Gerhard Hilt
Abstract
Indium tribromide catalysed the transfer hydrogenation from dihydroaromatic compounds, such as the commercially available γ-terpinene, to enones, which resulted in the cyclisation to trisubstituted furan derivatives. The reaction was initiated by a Michael addition of a hydride nucleophile to the enone subunit followed by a Lewis-acid-assisted cyclisation and the formation of a furan-indium intermediate and a Wheland intermediate derived from the dihydroaromatic starting material. The product was formed by protonation from the Wheland complex and replaced the indium tribromide substituent. In addition, a site-specific deuterium labelling of the dihydroaromatic HD surrogates resulted in site specific labelling of the products and gave useful insights into the reaction mechanism by H-D scrambling.