UCL logo

UCL Discovery

UCL home » Library Services » Electronic resources » UCL Discovery

An Alternative Approach to Aldol Reactions: Gold-Catalyzed Formation of Boron Enolates from Alkynes

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. Green open access

[img]
Preview
PDF - Requires a PDF viewer such as GSview, Xpdf or Adobe Acrobat Reader
50Kb

Abstract

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.

Type:Article
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
DOI:10.1021/ja102129c
Publisher version:http://dx.doi.org/10.1021/ja102129c
Language:English
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

View download statistics for this item

Archive Staff Only: edit this record