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A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons.

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 ?,?-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 ?,?-unsaturated acylboronate.

SUBMITTER: Lin S

PROVIDER: S-EPMC6495705 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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A modular and concise approach to MIDA acylboronates <i>via</i> chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons.

Lin Shengjia S Wang Lucia L Aminoleslami Negin N Lao Yanting Y Yagel Chelsea C Sharma Abhishek A

Chemical science 20190321 17

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 acylb ...[more]

PMID: 31123579

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