Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Iridium-Catalyzed Isomerization/Bromination of Allylic Alcohols: Synthesis of alpha-Bromocarbonyl Compounds
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Show others and affiliations
2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 34, 10703-10709 p.Article in journal (Refereed) Published
Abstract [en]

alpha-Brominated ketones and aldehydes, with two adjacent electrophilic carbon atoms, are highly valuable synthetic intermediates in organic synthesis, however, their synthesis from unsymmetrical ketones is very challenging, and current methods suffer from low selectivity. We present a new, reliable, and efficient method for the synthesis of alpha-bromocarbonyl compounds in excellent yields and with excellent selectivities. Starting from allylic alcohols as the carbonyl precursors, the combination of a 1,3-hydrogen shift catalyzed by iridium(III) with an electrophilic bromination gives alpha-bromoketones and aldehydes in good to excellent yields. The selectivity of the process is determined by the structure of the starting allylic alcohol; thus, alpha-bromoketones formally derived from unsymmetrical ketones can be synthesized in a straightforward and selective manner.

Place, publisher, year, edition, pages
2014. Vol. 20, no 34, 10703-10709 p.
Keyword [en]
allylic compounds, bromination, iridium, ketones, synthetic methods
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-107423DOI: 10.1002/chem.201402350ISI: 000340505500019OAI: oai:DiVA.org:su-107423DiVA: diva2:748609
Funder
Knut and Alice Wallenberg FoundationSwedish Research CouncilVINNOVAWenner-Gren Foundations
Note

AuthorCount:5;

Available from: 2014-09-19 Created: 2014-09-15 Last updated: 2017-11-09Bibliographically approved

Open Access in DiVA

fulltext(557 kB)2 downloads
File information
File name FULLTEXT01.pdfFile size 557 kBChecksum SHA-512
405caf0ba8d74eb70df328b217ad8e4e80d9edcae71239d4e05e7a114c192e1720939bf0388d0ec02106cbec70f657dce8c96c3b0ccc8b6ba630fa80c4538069
Type fulltextMimetype application/pdf

Other links

Publisher's full text

Search in DiVA

By author/editor
Bermejo Gomez, AntonioErbing, Elis
By organisation
Department of Organic Chemistry
In the same journal
Chemistry - A European Journal
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar
Total: 2 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 104 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf