The importance of the Lewis base in lithium mediated metallation and bond cleavage reaction of allyl amines and allyl phosphines

V. L. Blair, M. A. Stevens, C. D. Thompson

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Metallation of two analogous N- and P-allyl molecules Ph2NCH2CHCH21 and Ph2PCH2CHCH22 with nBuLi have shown contrasting reactivities based on the choice of Lewis donor. With 1 metallation of the alpha carbon atom was achieved regardless of the Lewis donor used while in comparison metallation of 2 showed an unexpected donor denticity dependence with P-C bond clevage induced with the tri-dentate PMDETA. Complementary DFT and solution studies rationalise this outcome.

Original languageEnglish
Pages (from-to)8111-8114
Number of pages4
JournalChemical Communications
Issue number52
Publication statusPublished - 2016

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