Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing Groups

• Published in: Journal of the American Chemical Society Vol. 128; no. 25; pp. 8150 - 8151
• Main Authors: Sebelius, Sara, Olsson, Vilhelm J, Wallner, Olov A, Szabó, Kálmán J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.06.2006; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Kemi; NATURAL SCIENCES; NATURVETENSKAP; Organic chemistry; Organisk kemi; Physical Sciences; Science & Technology; SRA - Molecular Bioscience; SRA - Molekylär biovetenskap; DISPLACEMENT; LIGANDS; ALKYLATION; COMPLEXES; ESTERS
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/ja062585o

Palladium-catalyzed coupling reactions of functionalized allylboronic acids with iodobenzenes were achieved under standard Suzuki−Miyaura coupling conditions. The coupling reactions afforded selectively the branched allylic products in high to excellent yields. In contrast to palladium-catalyzed nucleophilic substitution reactions proceeding via (η3-allyl)palladium intermediates, this process does not require directing groups in the allyl moiety to achieve substitution at the congested allylic terminus. The regioselectivity of the process was largely unaffected by the substituent effects of the iodobenzenes and the allylic substrates.