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Air stable, phosphine-free anionic palladacyclopentadienyl catalysts: Remarkable halide and pseudohalide effects in Stille coupling

Crawforth, C.M., Fairlamb, I.J.S., Kapdi, A.R., Serrano, J.L., Taylor, R.J.K. and Sanchez, G. (2006) Air stable, phosphine-free anionic palladacyclopentadienyl catalysts: Remarkable halide and pseudohalide effects in Stille coupling. Advanced Synthesis & Catalysis, 348 (4-5). pp. 405-412. ISSN 1615-4150

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Abstract

The Stille cross-coupling of allylic and benzyl bromides is shown to proceed efficiently using phosphine-free dinuclear anionic palladacyclopentadienyl catalysts possessing bridging (N,O)-imidate ligands. The type of bridging anion influences the catalytic activity considerably. Halide anions such as chloride, bromide or iodide also influence the catalytic activity but to a far lesser extent than the pseudohalide imidate anions (from succinimide or phthalimide). A Baldwin-type cooperative effect is seen with 7a using CuI as a co-catalyst, in the presence of two equivalents of CsF in DMF at 40 °C. In toluene, these additives slow down substrate turnover.

Item Type: Article
Keywords: CC bond formation • copper(I) salts • cross-coupling • halide effects • palladium
Academic Units: The University of York > Chemistry (York)
Depositing User: York RAE Import
Date Deposited: 14 Aug 2009 12:53
Last Modified: 14 Aug 2009 12:53
Published Version: http://dx.doi.org/10.1002/adsc.200505325
Status: Published
Publisher: John Wiley & Sons
Identification Number: 10.1002/adsc.200505325
URI: http://eprints.whiterose.ac.uk/id/eprint/5562

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