A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons. Issue 17 (2nd April 2019)

• Record Type: Journal Article
• Authors: Lin, Shengjia; Wang, Lucia; Aminoleslami, Negin; Lao, Yanting; Yagel, Chelsea; Sharma, Abhishek
• Is Part Of: Chemical science. Volume 10:Issue 17(2019)
• Page Start: 4684
• Page End: 4691
• Publication Date: 2019-04-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc00378a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Novel and mild synthesis of MIDA acylboronates including a novel class of acylborons and first chemoselective oxidation of geminal diborylalkanes. Abstract : 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 α, β-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 α, β-unsaturated acylboronate.