Metal-free direct amination/aromatization of 2-cyclohexenones to iodo-N-arylanilines and N-arylanilines promoted by iodine

Christopher Maycock

doi:10.1039/c2cc35801h

Metal-free direct amination/aromatization of 2-cyclohexenones to iodo-N-arylanilines and N-arylanilines promoted by iodine

Christopher Maycock

Instituto de Tecnologia Química e Biológica António Xavier (ITQB)

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

64 Citations (Scopus)

Abstract

An iodine mediated aromatization leading to a one-pot synthesis of iodo-N-arylanilines and N-arylanilines is reported. This highly regioselective aliphatic-aromatic transformation can be performed with various combinations of 2-cyclohexenones and anilines. The presence of a directing group is crucial for achieving high yields.

Original language	Unknown
Pages (from-to)	10901-10903
Journal	Chemical Communications
Volume	48
Issue number	88
DOIs	https://doi.org/10.1039/c2cc35801h
Publication status	Published - 1 Jan 2012

Access to Document

10.1039/c2cc35801h

Cite this

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abstract = "An iodine mediated aromatization leading to a one-pot synthesis of iodo-N-arylanilines and N-arylanilines is reported. This highly regioselective aliphatic-aromatic transformation can be performed with various combinations of 2-cyclohexenones and anilines. The presence of a directing group is crucial for achieving high yields.",

keywords = "SOLVENT-FREE IODINATION, AROMATIC-COMPOUNDS, ARYLATION, ENAMINES, OXIDATIVE IODINATION, EFFICIENT, ACID, REAGENT SYSTEM, AMINES, ARENES",

author = "Christopher Maycock",

year = "2012",

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day = "1",

doi = "10.1039/c2cc35801h",

language = "Unknown",

volume = "48",

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journal = "Chemical Communications",

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publisher = "RSC - Royal Society of Chemistry",

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AU - Maycock, Christopher

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Y1 - 2012/1/1

N2 - An iodine mediated aromatization leading to a one-pot synthesis of iodo-N-arylanilines and N-arylanilines is reported. This highly regioselective aliphatic-aromatic transformation can be performed with various combinations of 2-cyclohexenones and anilines. The presence of a directing group is crucial for achieving high yields.

AB - An iodine mediated aromatization leading to a one-pot synthesis of iodo-N-arylanilines and N-arylanilines is reported. This highly regioselective aliphatic-aromatic transformation can be performed with various combinations of 2-cyclohexenones and anilines. The presence of a directing group is crucial for achieving high yields.

KW - SOLVENT-FREE IODINATION

KW - AROMATIC-COMPOUNDS

KW - ARYLATION

KW - ENAMINES

KW - OXIDATIVE IODINATION

KW - EFFICIENT

KW - ACID

KW - REAGENT SYSTEM

KW - AMINES

KW - ARENES

U2 - 10.1039/c2cc35801h

DO - 10.1039/c2cc35801h

M3 - Article

SN - 1359-7345

VL - 48

SP - 10901

EP - 10903

JO - Chemical Communications

JF - Chemical Communications

IS - 88

ER -