We developed simple and efficient protocols for palladium-catalyzed regioselective a-a nd b-arylations of structurally diverse vinyl ethers.B oth catalytic methods proceed under relatively mild reactions conditions applying to abroad substrate range including more complex compounds providing arylated glucal or isochromene.L acking the common requirement of alarge reagent excess,the transformations are highly economic and limiting the waste production. Results from computational studies (DFT) provided insight into the key factors determining the pronounced regioselectivities of the investigated reactions.
We developed simple and efficient protocols for palladium‐catalyzed regioselective α‐ and β‐arylations of structurally diverse vinyl ethers. Both catalytic methods proceed under relatively mild reactions conditions applying to a broad substrate range including more complex compounds providing arylated glucal or isochromene. Lacking the common requirement of a large reagent excess, the transformations are highly economic and limiting the waste production. Results from computational studies (DFT) provided insight into the key factors determining the pronounced regioselectivities of the investigated reactions.
A direct, effective, and operationally simple transformation of esters into ketones or alkenes by the exclusive action of Tebbe’s reagent has been developed. The transformation utilizes the dual character of Tebbe’s reagent as both a methylenation agent and a rearrangement catalyst in the reaction of a wide range of substituted vinyl ethers. The resulting transformation involves sequential methylenation and rearrangement reactions and it offers a high degree of selectivity toward the synthesis of ketones or alkenes. The scope and limitations of the developed methods have been also examined.
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