Abstract
We present here our results on the temperature controlled, selective hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes with nucleophilic species of selenium, tellurium and sulfur generated in situ from the respective diaryl dichalcogenide and NaBH4. Using polyethylene glycol (PEG)-400 at 30 oC the (Z)-chalcogenoenynes are obtained and at 90 oC the (Z,Z)-bis-chalcogen-1,3-butadienes are produced in good to excellent yields. Alternatively to conventional oil bath heating, the use of microwave irradiation is also presented as an alternative energy source that provides the expected products in few minutes.
Highlights
Enynes, dienes and related unsaturated structures are key fragments found in a diverse array of natural products.[1]
Bombykol contains conjugated olefins of E,Z-configuration and represents a milestone on the structural elucidation of a natural compound important for chemical interactions between live organisms.[3]. These unsaturated structures represent important moieties found in a diverse array of biologically active compounds,[4] for example the drug lovastatin, an important 3-hydroxy-3methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitor and antihypercholesterolemic agent that has a diene portion in its structure.[5]
We describe our results on the hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes 1 under mild reaction conditions using diaryl dichalcogenides 2 and polyethylene glycol (PEG)-400 as solvent (Scheme 1)
Summary
Dienes and related unsaturated structures are key fragments found in a diverse array of natural products.[1] A widely studied example is the naturally occurring pheromone bombykol, isolated from the silkworm moth (Bombyx mori), which was firstly characterized by Butenandt et al.[2] over 40 years ago. Bombykol contains conjugated olefins of E,Z-configuration and represents a milestone on the structural elucidation of a natural compound important for chemical interactions between live organisms.[3] these unsaturated structures represent important moieties found in a diverse array of biologically active compounds,[4] for example the drug lovastatin, an important 3-hydroxy-3methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitor and antihypercholesterolemic agent that has a diene portion in its structure.[5]. These methods are undeniably efficient, protocols using stable and handled materials for rigorous regio- and stereochemical controlled synthesis remains a challenge
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