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DOI: 10.1055/s-0028-1083456
Direct Pd-Catalyzed Acylation of Aryl Bromides with Aldehydes
Contributor(s):Paul Knochel, Andrei GavryushinUniversity of Liverpool, UK
Direct Acylation of Aryl Bromides with Aldehydes by Palladium Catalysis
J. Am. Chem. Soc. 2008, 130: 10510-10511
Publication History
Publication Date:
23 October 2008 (online)
Key words
aryl bromides - aryl ketones - palladium catalysis
Significance
Aryl alkyl ketones are among the most important intermediates in chemical industry. The main preparation method, the Friedel-Crafts acylation, is rather limited in substrate scope. The authors disclose herein a simple, efficient and versatile method for the preparation of these compounds starting from aryl and heteroaryl bromides and aldehydes. The protocol is easy to perform, does not require expensive ligands and allows using highly functionalized substrates.
Comment
The reaction proceeds via the formation of an enamine, which then undergoes a Heck reaction, followed by hydrolysis. The enamine intermediate can be isolated and involved in the same reaction. Other phosphines like PPh3 or DPPF are also efficient ligands for Pd in this reaction. Interestingly, under similar conditions but in the absence of pyrrolidine, this reaction gives α-arylated aldehydes (G. D. Vo, J. F. Hartwig Angew. Chem. Int. Ed. 2008, 47, 2127.)