Abstract
Three methods have been developed for generating alkynylsamariums: (1) reduction of iodoalkynes with SmI 2 in the presence of HMPA, (2) deprotonation at the terminal position of 1-alkynes either by tetrahydrofurylsamarium generated by PhI and SmI 2 in THF, or, (3) deprotonation by butyllithium followed by metal–metal exchange with SmI 3. Alkynylsamariums arising from iodoalkynes with SmI 2 undergo coupling with carbonyl compounds under both Barbier and Grignard conditions in benzene-HMPA or THF-HMPA as a solvent system. Tetrahydrofurylsamarium generated from iodobenzene and SmI 2 in THF can deprotonate from terminal alkynes to yield alkynylsamariums whereas other alkylsamariums, such as ethyl-, isopropyl-, cyclohexyl-, and cyclopentylsamarium do not work well. Metal–metal exchange between an alkynyllithium and SmI 3 is also effective; the reactive species in this case would be alkynylsamariums rather than alkynyllithiums. To reveal the properties of alkynylsamariums, we examined the stability and reactivity of alkynylsamariums toward various electrophiles.
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