Aryne-Enabled C-N Arylation of Anilines

Thomas Sephton; Anastasios Charitou; Cristina Trujillo Del Valle; Jonathan M. Large; Sam Butterworth; Michael Greaney

doi:10.1002/anie.202310583

Aryne-Enabled C-N Arylation of Anilines

Thomas Sephton, Anastasios Charitou, Cristina Trujillo Del Valle, Jonathan M. Large, Sam Butterworth, Michael Greaney

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

Abstract

Anilines are potentially high-value arylating agents, but are limited by the low reactivity of the strong C-N bond. We show that the reactive intermediate benzyne can be used to both activate anilines, and set up an aryl transfer reaction in a single step. The reaction does not require any transition metal catalysts or stoichiometric organometallics, and establishes a metal-free route to valuable biaryl products by functionalizing the aniline C-N bond.

Original language	English
Article number	e202310583
Number of pages	7
Journal	Angewandte Chemie. International Edition
Volume	62
Issue number	49
Early online date	18 Oct 2023
DOIs	https://doi.org/10.1002/anie.202310583
Publication status	Published - 4 Dec 2023

Keywords

C−N arylation
Smiles rearrangement
aniline
aryne
biaryl synthesis

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10.1002/anie.202310583Licence: CC BY

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abstract = "Anilines are potentially high-value arylating agents, but are limited by the low reactivity of the strong C-N bond. We show that the reactive intermediate benzyne can be used to both activate anilines, and set up an aryl transfer reaction in a single step. The reaction does not require any transition metal catalysts or stoichiometric organometallics, and establishes a metal-free route to valuable biaryl products by functionalizing the aniline C-N bond.",

keywords = "C−N arylation, Smiles rearrangement, aniline, aryne, biaryl synthesis",

author = "Thomas Sephton and Anastasios Charitou and {Trujillo Del Valle}, Cristina and Large, {Jonathan M.} and Sam Butterworth and Michael Greaney",

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T1 - Aryne-Enabled C-N Arylation of Anilines

AU - Sephton, Thomas

AU - Charitou, Anastasios

AU - Trujillo Del Valle, Cristina

AU - Large, Jonathan M.

AU - Butterworth, Sam

AU - Greaney, Michael

PY - 2023/12/4

Y1 - 2023/12/4

N2 - Anilines are potentially high-value arylating agents, but are limited by the low reactivity of the strong C-N bond. We show that the reactive intermediate benzyne can be used to both activate anilines, and set up an aryl transfer reaction in a single step. The reaction does not require any transition metal catalysts or stoichiometric organometallics, and establishes a metal-free route to valuable biaryl products by functionalizing the aniline C-N bond.

AB - Anilines are potentially high-value arylating agents, but are limited by the low reactivity of the strong C-N bond. We show that the reactive intermediate benzyne can be used to both activate anilines, and set up an aryl transfer reaction in a single step. The reaction does not require any transition metal catalysts or stoichiometric organometallics, and establishes a metal-free route to valuable biaryl products by functionalizing the aniline C-N bond.

KW - C−N arylation

KW - Smiles rearrangement

KW - aniline

KW - aryne

KW - biaryl synthesis

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M3 - Article

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JF - Angewandte Chemie. International Edition

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ER -

Aryne-Enabled C-N Arylation of Anilines

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Aryne-Enabled C-N Arylation of Anilines

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