Journal
CHEMICAL SCIENCE
Volume 10, Issue 17, Pages 4684-4691Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc00378a
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- Stevens Institute of Technology
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Acylboronates represent a very intriguing and rare class of organoboronates. Synthesis of these compounds from readily available substrates under mild conditions and access to novel classes of acylborons has been challenging. We report a novel and concise route to various MIDA acylboronates from terminal alkynes/ alkenes or vinyl boronic esters using unsymmetrical geminal diborylalkanes as key intermediates. The high modularity and mild conditions of this strategy allowed a facile access to acylboronates possessing aliphatic, aromatic as well as the rarer heteroaromatic, alkynyl and alpha,beta-unsaturated scaffolds. To the best of our knowledge, this is the first report of chemoselective oxidation of geminal diborons as well as synthesis of an alpha,beta-unsaturated acylboronate.
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