Journal
ORGANIC LETTERS
Volume 19, Issue 16, Pages 4291-4294Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01950
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Funding
- NSFC [21325208, 21572212]
- Ministry of Science and Technology of China [2017YFA0303500]
- CAS [XDB20000000]
- Key Technologies R&D Programme of Anhui Province [1604a0702027]
- FRFCU
- PCSIRT
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Decarboxylative borylation of aryl and alkenyl carboxylic acids with bis(pinacolato)diboron was achieved through N-hydroxyphthalimide esters using tert-butyl isonicotinate as a catalyst under base-free conditions. A variety of aryl carboxylic acids possessing different functional groups and electronic properties can be smoothly converted to aryl boronate esters, including those that are difficult to decarboxylate under transition-metal catalysis, offering a new method enabling use of carboxylic acid as building blocks in organic synthesis. Mechanistic analysis suggests the reaction proceeds through coupling of a transient aryl radical generated by radical decarboxylation with a pyridine-stabilized persistent boryl radical. Activation of redox active esters may proceed via an intramolecular single-electron-transfer (SET) process through a pyridine-diboron-phthalimide adduct and accounts for the base-free reaction conditions.
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