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Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C-C-Coupling Reactions

  • The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.

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Metadaten
Author:Bernd SchmidtORCiDGND, Nelli Elizarov, Uwe SchildeORCiDGND, Alexandra Kelling
DOI:https://doi.org/10.1021/acs.joc.5b00272
ISSN:0022-3263 (print)
Pubmed Id:http://www.ncbi.nlm.nih.gov/pubmed?term=25700158
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:2015
Year of Completion:2015
Release Date:2017/03/27
Volume:80
Issue:9
Pagenumber:12
First Page:4223
Last Page:4234
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert