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Highly Efficient Pd-Catalyzed Carbonylative Cross-Coupling Reactions with Tetraorganoindates

Sung Wook Lee, Kooyeon Lee, Dong Seomoon, Sundae Kim, Hyunseok Kim, Hyun Kim, Eunkyong Shim, Miae Lee, Seokju Lee, Misook Kim, and Phil Ho Lee*

*Department of Chemistry, Kangwon National University, Chunchon 200-701, Republic of Korea, Email: phleekangwon.ac.kr

S. W. Lee, K. Lee, D. Seomoon, S. Kim, H. Kim, H. Kim, E. Shim, M. Lee, J. Org. Chem., 2004, 69, 4852-4855.

DOI: 10.1021/jo0495790


Abstract

Tetraorganoindates, which are easily prepared from 1 eq. of InCl3 and 4 eq. of organometallics, could be employed as effective nucleophilic cross-coupling partners in Pd-catalyzed carbonylative cross-coupling reactions with a variety of electrophiles under a carbon monoxide atmosphere. The present method gave unsymmetrical ketones in good yields.

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Details

The document discusses a study on highly efficient Pd-catalyzed carbonylative cross-coupling reactions using tetraorganoindates as nucleophilic partners. These reactions, conducted under a carbon monoxide atmosphere in THF at 60°C, produce unsymmetrical ketones and 1,4-diacylbenzenes in good yields. Tetraorganoindates, prepared from InCl3 and organometallics, exhibit high reactivity, efficiency, and versatility. The study optimized the reaction conditions, finding that 0.28 mol of tetra-n-butylindate with 4 mol% of Pd(PPh3)4 yielded the best results. Various alkyl and aryl groups on tetraorganoindates were tested, showing little effect on reaction rates or yields. The method was also effective with different electrophiles, including aryl iodides, vinyl halides, and benzoyl chloride. The study highlights the advantages of using tetraorganoindates over other organometallic reagents, such as ease of preparation, high reactivity, and mild reaction conditions. The research was supported by the Korea Science & Engineering Foundation and the CMDS at KAIST, with experimental procedures and characterization data available online.


Key Words

Ketones, Aryl ketones, Palladium, Catalysis


ID: J42-Y2004-580