Metal Free Synthesis of Secondary Arylamines: An Aliphatic to Aromatic Transformation

Maria Teresa Barros; Christopher Maycock

doi:10.1002/ejoc.201201263

Metal Free Synthesis of Secondary Arylamines: An Aliphatic to Aromatic Transformation

Maria Teresa Barros, Christopher Maycock

Research output: Contribution to journal › Article

10 Citations (Scopus)

Abstract

An efficient method for the N‐arylation of primary and some secondary amines using 2‐halocyclohex‐2‐enones in an aliphatic‐to‐aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed. A series of arylamines have been synthesized from 2‐halocyclohex‐2‐enones by in situ enamine formation followed by aromatization under environmentally friendly conditions using pTsOH. This metal‐free, practical, relatively inexpensive protocol is of value in organic synthesis for industrial and academic applications.

Original language	English
Pages (from-to)	742-747
Journal	European Journal of Organic Chemistry
Issue number	4
DOIs	https://doi.org/10.1002/ejoc.201201263
Publication status	Published - 1 Feb 2013

Access to Document

10.1002/ejoc.201201263

Fingerprint Dive into the research topics of 'Metal Free Synthesis of Secondary Arylamines: An Aliphatic to Aromatic Transformation'. Together they form a unique fingerprint.

Cite this

@article{5fe2b191e748402397e06ceec89bf01b,

title = "Metal Free Synthesis of Secondary Arylamines: An Aliphatic to Aromatic Transformation",

abstract = "An efficient method for the N‐arylation of primary and some secondary amines using 2‐halocyclohex‐2‐enones in an aliphatic‐to‐aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed. A series of arylamines have been synthesized from 2‐halocyclohex‐2‐enones by in situ enamine formation followed by aromatization under environmentally friendly conditions using pTsOH. This metal‐free, practical, relatively inexpensive protocol is of value in organic synthesis for industrial and academic applications.",

keywords = "Metal-free reactions, Synthetic methods, Amines, Green chemistry, Enones, Arylation",

author = "Barros, {Maria Teresa} and Christopher Maycock",

year = "2013",

month = feb,

day = "1",

doi = "10.1002/ejoc.201201263",

language = "English",

pages = "742--747",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "4",

}

TY - JOUR

T1 - Metal Free Synthesis of Secondary Arylamines: An Aliphatic to Aromatic Transformation

AU - Barros, Maria Teresa

AU - Maycock, Christopher

PY - 2013/2/1

Y1 - 2013/2/1

N2 - An efficient method for the N‐arylation of primary and some secondary amines using 2‐halocyclohex‐2‐enones in an aliphatic‐to‐aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed. A series of arylamines have been synthesized from 2‐halocyclohex‐2‐enones by in situ enamine formation followed by aromatization under environmentally friendly conditions using pTsOH. This metal‐free, practical, relatively inexpensive protocol is of value in organic synthesis for industrial and academic applications.

AB - An efficient method for the N‐arylation of primary and some secondary amines using 2‐halocyclohex‐2‐enones in an aliphatic‐to‐aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed. A series of arylamines have been synthesized from 2‐halocyclohex‐2‐enones by in situ enamine formation followed by aromatization under environmentally friendly conditions using pTsOH. This metal‐free, practical, relatively inexpensive protocol is of value in organic synthesis for industrial and academic applications.

KW - Metal-free reactions

KW - Synthetic methods

KW - Amines

KW - Green chemistry

KW - Enones

KW - Arylation

U2 - 10.1002/ejoc.201201263

DO - 10.1002/ejoc.201201263

M3 - Article

SP - 742

EP - 747

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 4

ER -