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Indium-Catalysed Transfer Hydrogenation for the Reductive Cyclisation of 2-Alkynyl Enones towards Trisubstituted Furans.


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.

SUBMITTER: Li L 

PROVIDER: S-EPMC8597135 | biostudies-literature |

REPOSITORIES: biostudies-literature

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