Since the discovery of Suzuki-Miyaura cross-coupling, organoboron compounds have become a valuable class of synthetic intermediates in modern synthesis. As a result, it is imperative to both develop new methodology that enables the rapid synthesis of highly functionalized organoboron compounds and investigate additional chemistry associated with their derivatives. In recent work,1we demonstrated allyl sulfones bearing a boronic ester at the 2-position could be alkylated without decomposition of the Lewis-acidic boron moiety. The ability of the boronic ester to tolerate anion formation permitted the synthesis of alkylated products that could undergo further transformations. In this work, functionalized cyclic systems bearing vinyl organoboron species are generated via ruthenium-catalyzed intramolecular ring-closing metathesis (RCM) of alkylated products. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/239nm/uploads/6046_acs_fig.jpg' alt='' /> 1. Altenhofer, E.; Harmata, M. Chem. Commun. 2013 , 49, 2365-2367.

Synthesis of functionalized ring systems containing boron functionality

246th National Meeting (2013)

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