Boronic derivatives are one of the most successful and important reagents for organic synthesis and especially for drug discovery programs using the catalyzed Suzuki-Miyaura and Chan-Lam cross-coupling reactions. The majority of these reagents are based on sp<sup>2</sup> aromatic, heteroaromatic and vinylboronic compounds. There is a growing interest in preparing functionalized alkylboronic compounds. Recently we discovered a remarkable property of dicyclohexylborane. This reagent rapidly hydroborates functionalized terminal alkenes without reduction of the functional group. Avoiding the necessity of protecting and deprotecting reactive groups. The cyclohexyl groups are selectively removed by reductive alkylation with two equivalents of <i>p</i>-benzoquinone and the resultant boronic esters are converted into the functionalized potassium trifluoroborate salt in very good to excellent yields. In this study, we will report our efforts in preparing the potassium alkylphosphonate trifluoroborates salts via hydroboration of terminal alkenylphosphonic esters. These compounds have potential biological applications as well as potent applications in organic synthesis.

Synthesis of potassium trifluoroalkylphosphosphonates via hydroboration of vinylphosphonates

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.