Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

SCImago Journal Rank (SJR) 2017: 1.212
Source Normalized Impact per Paper (SNIP) 2017: 1.546

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 84, Issue 11

Issues

Complexity-generating hydration reactions via gold-catalyzed addition of boronic acids to alkynes

Tom D. Sheppard
  • Corresponding author
  • Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon St, London, WC1H 0AJ, UK
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2012-06-24 | DOI: https://doi.org/10.1351/PAC-CON-12-01-08

Boronic acids can serve as organic soluble substitutes for water molecules in the metal-catalyzed hydration of alkynes. The Au-catalyzed addition of boronic acids to alkynes provides an alternative method for enolate generation, which proceeds under exceptionally mild conditions. The resulting enolates can be trapped by aldehydes present in the reaction mixture, giving aldol products that can be isolated as cyclic borate esters. These compounds are versatile synthetic intermediates that can be elaborated into a variety of products by transformation of the boron moiety. The Au-catalyzed reaction of boronic acids with propargylic alcohols results in efficient Meyer–Schuster rearrangement to the corresponding enones. The rearrangement of tertiary alcohols gives (E)-enones with moderate to good selectivity, and the addition of a boronic acid to the reaction appears to enhance the level of geometrical control. The rearrangement of primary alcohols to terminal enones also occurs readily in the presence of catalytic Au(I) and a boronic acid, and the resulting terminal enones can be reacted with nucleophiles in one-pot procedures to give a variety of β-substituted ketones.

Keywords: aldol reactions; alkynes; boron; gold; rearrangements

Conference

International Meeting on Boron Chemistry (IMEBORON-XIV), International Symposium on Boron Chemistry, IMEB, Boron Chemistry, 14th, Niagara Falls, Canada, 2011-09-11–2011-09-15

References

About the article

Published Online: 2012-06-24

Published in Print: 2012-06-24


Citation Information: Pure and Applied Chemistry, Volume 84, Issue 11, Pages 2431–2441, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-12-01-08.

Export Citation

© 2013 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[2]
Gaj Stavber and Zdenko Časar
ChemCatChem, 2014, Volume 6, Number 8, Page 2162

Comments (0)

Please log in or register to comment.
Log in