Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 17, Pages 5968-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja102129c
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Funding
- EPSRC
- DAAD
- Engineering and Physical Sciences Research Council [EP/E052789/1] Funding Source: researchfish
- EPSRC [EP/E052789/1] Funding Source: UKRI
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A new method for enolate generation via the gold-catalyzed addition of boronic acids to alkynes is reported. The formation of boron enolates from readily accessible ortho-alkynylbenzeneboronic acids proceeds rapidly with 2 mol % PPh3AuNTf2 at ambient temperature. The enolates undergo aldol reaction with an aldehyde present in the reaction mixture to give cyclic boronate esters, which can be subsequently transformed into phenols, biaryls, or dihydrobenzofurans via oxidation, Suzuki-Miyaura, or intramolecular Chan-Lam coupling, respectively. A combined gold/boronic acid catalyzed aldol condensation reaction of an alkynyl aldehyde was also successfully achieved.
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