Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant

A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required....

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2019-05, Vol.55 (45), p.6445-6448
Hauptverfasser: Quibell, Jacob M, Duan, Guojian, Perry, Gregory J. P, Larrosa, Igor
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Sprache:eng
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Zusammenfassung:A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non- ortho -substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives. A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling of carboxylic acids with arylboronic acids has been developed.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc01817d