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A 2-pyrone cycloaddition route to functionalised aromatic boronic esters

2007; Elsevier BV; Volume: 64; Issue: 5 Linguagem: Inglês

10.1016/j.tet.2007.08.118

1464-5416

Patrick M. Delaney, Duncan L. Browne, Harry Adams, Andrew Plant, Joseph P. A. Harrity,

Catalytic Cross-Coupling Reactions

A [4+2] cycloaddition/retro-cycloaddition route to functionalised aromatic boronic esters is outlined. A range of electron deficient dienes (2-pyrones) and dienophiles (alkynylboronates) were found to participate in the reaction. Furthermore, high levels of regiocontrol could be obtained in this process and a consistent mode of alkyne insertion has been uncovered.