Korner, C; Starkov, P; Sheppard, TD; (2010) An Alternative Approach to Aldol Reactions: Gold-Catalyzed Formation of Boron Enolates from Alkynes. [Rapid communication]. Journal of the American Chemical Society , 132 (17) 5968 -5969. 10.1021/ja102129c.
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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.
|Title:||An Alternative Approach to Aldol Reactions: Gold-Catalyzed Formation of Boron Enolates from Alkynes|
|Open access status:||An open access version is available from UCL Discovery|
|Additional information:||Copyright © 2010 American Chemical Society. Article made available here by permission from publisher for noncommercial purposes. The article as published is available via http://pubs.acs.org/articlesonrequest/AOR-ffRktq44n73F9AsqbW3u|
|Keywords:||PHENYLBORONIC ACIDS, CUPRIC ACETATE, CYCLOISOMERIZATION, ARYLATION, ALCOHOLS, ETHERS, ISOMERIZATION, ACETALDEHYDE, DERIVATIVES, ADDITIONS|
|UCL classification:||UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry|
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