Development of synthetic strategies toward vinylboronates
(2025)
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- Boron chemistry has witnessed major achievements over the last decades to belong now to the standard toolbox of organic chemists. This is attributed to the ease of access to organoboron compounds and their efficient conversion into a wide array of diverse functional groups. Notably, vinylboronates have garnered significant attention as highly reactive substrates in Suzuki-Miyaura cross-coupling reactions. Boron compounds have also stimulated the interest of the pharmaceutical industry for various applications. Given the high demand for these compounds, there is an increasing need for a wider variety of synthetic methods. Our long-term goal is the synthesis of borylated exo-glycals; exo-glycals being the subject of growing research interest for their synthetic and biochemical significance. However, the preparation of borylated exo-glycals first requires the development of suitable borylating olefination strategies. Herein we report our efforts to develop new synthetic methods for vinylboronates, and to extend the existing ones to borylated exo-glycals. We began our investigations by considering the borylation of methylene exo-glycals via C-H activation or olefin metathesis. We then focused on the olefination reactions of readily available sugar lactones, such as the boron-Wittig reaction and the silica-based Peterson olefination. Experimental and computational studies were conducted to deepen our understanding of these olefination processes. In addition, Borylated phosphonium salts and borylated sulfones were synthesized in an effort to develop vinylboronate-compatible Wittig and modified Julia reactions
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Janssens, J. (2025). Development of synthetic strategies toward vinylboronates. https://hdl.handle.net/2078.5/274309