Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation

Jonathan Clayden; Hazel Turner; Mark Pickworth; Thomas Adler

doi:10.1021/ol0508025

Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation

Jonathan Clayden^*, Hazel Turner, Mark Pickworth, Thomas Adler

^*Corresponding author for this work

School of Chemistry

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

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) Unsymmetrical N,N′-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.

Original language	English
Pages (from-to)	3147-3150
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	15
Early online date	29 Jun 2005
DOIs	https://doi.org/10.1021/ol0508025
Publication status	Published - 21 Jul 2005

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Organic & Biological

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title = "Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation",

abstract = "(Chemical Equation Presented) Unsymmetrical N,N′-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.",

author = "Jonathan Clayden and Hazel Turner and Mark Pickworth and Thomas Adler",

year = "2005",

month = jul,

day = "21",

doi = "10.1021/ol0508025",

language = "English",

volume = "7",

pages = "3147--3150",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

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TY - JOUR

T1 - Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation

AU - Clayden, Jonathan

AU - Turner, Hazel

AU - Pickworth, Mark

AU - Adler, Thomas

PY - 2005/7/21

Y1 - 2005/7/21

N2 - (Chemical Equation Presented) Unsymmetrical N,N′-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.

AB - (Chemical Equation Presented) Unsymmetrical N,N′-diarylureas may be alkylated regioselectively at the more sterically congested nitrogen atom. The resulting mono-N-alkylated ureas undergo directed metalation (ortholithiation) with sec-BuLi to yield, on electrophilic quench, products functionalized regioselectively at the ring bearing the alkylated nitrogen atom.

UR - https://www.scopus.com/pages/publications/23044453131

U2 - 10.1021/ol0508025

DO - 10.1021/ol0508025

M3 - Article (Academic Journal)

C2 - 16018607

AN - SCOPUS:23044453131

SN - 1523-7060

VL - 7

SP - 3147

EP - 3150

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation

Abstract

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