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

doi:10.1039/c6cc03947b

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8111-8114
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	52
DOIs	https://doi.org/10.1039/c6cc03947b
Publication status	Published - 2016
Externally published	Yes

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title = "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.",

author = "Blair, {V. L.} and Stevens, {M. A.} and Thompson, {C. D.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

doi = "10.1039/c6cc03947b",

language = "English",

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pages = "8111--8114",

journal = "Chemical Communications",

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T1 - The importance of the Lewis base in lithium mediated metallation and bond cleavage reaction of allyl amines and allyl phosphines

AU - Blair, V. L.

AU - Stevens, M. A.

AU - Thompson, C. D.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84975852915&partnerID=8YFLogxK

U2 - 10.1039/c6cc03947b

DO - 10.1039/c6cc03947b

M3 - Article

SN - 1359-7345

VL - 52

SP - 8111

EP - 8114

JO - Chemical Communications

JF - Chemical Communications

IS - 52

ER -

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

Abstract

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