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Suzuki-Miyaura coupling of halophenols and phenol boronic acids: systematic investigation of positional isomer effects and conclusions for the synthesis of phytoalexins from Pyrinae

  • The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.

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Metadaten
Author:Bernd SchmidtORCiDGND, Martin Riemer
DOI:https://doi.org/10.1021/jo500675a
ISSN:0022-3263 (print)
Pubmed Id:http://www.ncbi.nlm.nih.gov/pubmed?term=24724893
Parent Title (English):The journal of organic chemistry
Publisher:American Chemical Society
Place of publication:Washington
Document Type:Article
Language:English
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
Volume:79
Issue:9
Pagenumber:15
First Page:4104
Last Page:4118
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert