Lithium Intermediates during the α‐Lithiation and Subsequent α‐Substitution of Heterocyclic Amines in the Presence of CO2

Sarah C. Ball; Ian Cragg‐Hine; Matthew G. Davidson; Robert P. Davies; Andrew J. Edwards; Isabel Lopez‐Solera; Paul R. Raithby; Ronald Snaith

doi:10.1002/anie.199509211

Lithium Intermediates during the α‐Lithiation and Subsequent α‐Substitution of Heterocyclic Amines in the Presence of CO₂

Sarah C. Ball, Ian Cragg‐Hine, Matthew G. Davidson, Robert P. Davies, Andrew J. Edwards, Isabel Lopez‐Solera, Paul R. Raithby, Ronald Snaith

University of Cambridge

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

Abstract

Two interdependent steps appear to be involved in the CO₂‐mediated electrophilic substitution of cyclic amines in the α position. The key finding is that the lithium carbamate 1 is not lithiated with tBuLi to any extent, but reacts only after addition of electrophiles like Me₃SiCl to give the desired α‐substitution product 2. (Figure Presented.)

Original language	English
Pages (from-to)	921-923
Number of pages	3
Journal	Angewandte Chemie International Edition in English
Volume	34
Issue number	8
DOIs	https://doi.org/10.1002/anie.199509211
Publication status	Published - 2 May 1995

Keywords

electrophilic substitution
heterocycles
lithiation
lithium compounds

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.199509211

Cite this

Ball, S. C., Cragg‐Hine, I., Davidson, M. G., Davies, R. P., Edwards, A. J., Lopez‐Solera, I., Raithby, P. R., & Snaith, R. (1995). Lithium Intermediates during the α‐Lithiation and Subsequent α‐Substitution of Heterocyclic Amines in the Presence of CO₂. Angewandte Chemie International Edition in English, 34(8), 921-923. https://doi.org/10.1002/anie.199509211

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abstract = "Two interdependent steps appear to be involved in the CO2‐mediated electrophilic substitution of cyclic amines in the α position. The key finding is that the lithium carbamate 1 is not lithiated with tBuLi to any extent, but reacts only after addition of electrophiles like Me3SiCl to give the desired α‐substitution product 2. (Figure Presented.)",

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AU - Davies, Robert P.

AU - Edwards, Andrew J.

AU - Lopez‐Solera, Isabel

AU - Raithby, Paul R.

AU - Snaith, Ronald

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KW - electrophilic substitution

KW - heterocycles

KW - lithiation

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