Development of a Cycloadditition Strategy to Aromatic Boronic Esters

• Main Author: Delaney, Patrick M.
• Published: University of Sheffield 2007
• Subjects: 547
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.486460

The cycloaddition reaction of alkynylboronates has been implemented in the facile synthesis of novel aromatic and heteroaromatic boronic esters. The use of pyranones in [4+2] cycloadditions with alkynylboronates led to the formation of aryl boronic esters. The scope of this cycloaddition has been realised and to some extent the regiochemical outcome, can be controlled by judicious positioning of electron deficient substituents on the pyranone substrate. The aryl boronic esters formed have successfully been shown to undergo Suzuki cross coupling reactions. The use of analogous dienes to pyranones has facilitated the synthesis of a range of highly functionalised pyridine and pyridone boronic esters. These pyridine and pyridone boronic esters formed have also been shown to partake in Suzuki cross coupling and carbon-boron bond oxidation reactions.