Facile Double-Lithiation of a Transient Urea: Vicarious ortho-Metalation of Aniline Derivatives

Chris E. Houlden; Guy C. Lloyd-Jones; Kevin I. Booker-Milburn

doi:10.1021/ol101102y

Facile Double-Lithiation of a Transient Urea: Vicarious ortho-Metalation of Aniline Derivatives

Chris E. Houlden, Guy C. Lloyd-Jones, Kevin I. Booker-Milburn

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

27 Citations (Scopus)

Abstract

A convenient one-pot method for the conversion of phenylisocyanate into ortho-functionalized aniline derivatives has been developed. The reaction proceeds via the selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithiophenylisocyanate, a highly improbable intermediate.

Original language	English
Pages (from-to)	3090-3092
Number of pages	3
Journal	Organic Letters
Volume	12
Issue number	13
DOIs	https://doi.org/10.1021/ol101102y
Publication status	Published - 2 Jul 2010

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DEVELOPMENT OF NEW PROTOCOLS FOR ALKENE DIFUNCTIONALISATION
Booker-Milburn, K. I. (Principal Investigator)
1/08/07 → 1/11/10
Project: Research

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title = "Facile Double-Lithiation of a Transient Urea: Vicarious ortho-Metalation of Aniline Derivatives",

abstract = "A convenient one-pot method for the conversion of phenylisocyanate into ortho-functionalized aniline derivatives has been developed. The reaction proceeds via the selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithiophenylisocyanate, a highly improbable intermediate.",

author = "Houlden, {Chris E.} and Lloyd-Jones, {Guy C.} and Booker-Milburn, {Kevin I.}",

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T1 - Facile Double-Lithiation of a Transient Urea: Vicarious ortho-Metalation of Aniline Derivatives

AU - Houlden, Chris E.

AU - Lloyd-Jones, Guy C.

AU - Booker-Milburn, Kevin I.

PY - 2010/7/2

Y1 - 2010/7/2

N2 - A convenient one-pot method for the conversion of phenylisocyanate into ortho-functionalized aniline derivatives has been developed. The reaction proceeds via the selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithiophenylisocyanate, a highly improbable intermediate.

AB - A convenient one-pot method for the conversion of phenylisocyanate into ortho-functionalized aniline derivatives has been developed. The reaction proceeds via the selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithiophenylisocyanate, a highly improbable intermediate.

U2 - 10.1021/ol101102y

DO - 10.1021/ol101102y

M3 - Article (Academic Journal)

C2 - 20527906

SN - 1523-7060

VL - 12

SP - 3090

EP - 3092

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Facile Double-Lithiation of a Transient Urea: Vicarious ortho-Metalation of Aniline Derivatives

Abstract

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DEVELOPMENT OF NEW PROTOCOLS FOR ALKENE DIFUNCTIONALISATION

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