Issue 52, 2016

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
11 May 2016
Accepted
27 May 2016
First published
31 May 2016

Chem. Commun., 2016,52, 8111-8114

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 and C. D. Thompson, Chem. Commun., 2016, 52, 8111 DOI: 10.1039/C6CC03947B

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