Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1127-1134
doi:10.1351/pac200880051127
Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes and alkenes*
Tetsuya Satoh, Kenji Ueura, and Masahiro Miura
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Abstract:
The oxidative coupling of benzoic acids with alkynes and alkenes effectively proceeds in the presence of a Rh catalyst and an appropriate oxidant to produce the corresponding isocoumarin and phthalide derivatives, respectively. Interestingly, by using an Ir catalyst in place of Rh, the acids and alkynes undergo 1:2 coupling accompanied by decarboxylation to afford naphthalene derivatives exclusively.
Keywords: C-C coupling; C-H bond cleavage; iridium; isocoumarin; naphthalene; oxidative coupling; phthalide; rhodium.
*Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194.