Insertion reactions of allenes with palladium aryl complexes [PdI(Ph)(PPh)] and PdI(Ph)(dppe)
Organometallics, ISSN: 0276-7333, Vol: 27, Issue: 11, Page: 2614-2626
2008
- 37Citations
- 16Captures
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Article Description
Treatment of [PdI(Ph)(PPh)] with allenes CH =C=CHR (R = CMe, COEt, P(O)(OEt) , and SOPh) in dichloromethane at room temperature produces a mixture of cis and trans isomers of the π-allyl palladium complexes PdI(η-CHC(Ph)CHR)(PPh) in which the R group is anti to the Ph group. The disubstituted alienes MeCH=C=CHR (R = P(O)(OEt) and SOPh) similarly react with [PdI(Ph)(PPh)] to give the π-allyl palladium complexes PdI(η-MeCHC(Ph)CHR)(PPh) in which the R group is anti and the Me group is syn to the Ph group. PdI(Ph)(dppe) alone was found to be unreactive toward allenes such as CH=C=CHSO Ph and MeCH=C=CHSOPh at room temperature. In contrast, in the presence of TIPF, PdI(Ph)(dppe) readily reacts with allenes CH=C=CHR (R = CMe, COEt, COPh, and SO Ph) and MeCH=C=CHSOPh to give the π-allyl palladium complexes [Pd(η-CHC(Ph)CHR)(dppe)]PF and [Pd(η-MeCHC(Ph)CHR)(dppe)]PF, respectively. Although mechanistically possible, vinyl complexes were not observed as the insertion products in all cases. The substituents of allenes appear to have no effect on the reaction pathways, at least for the allenes used in this study. The insertion reactions involving PdI(Ph)(PR)(allene) have been studied by computational chemistry using the model complex PdI(Ph)(MeCH=C= CHSOH)(PH). © 2008 American Chemical Society.
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