Mild and Practical Method for the α-Arylation of Nitriles with Heteroaryl Halides

A mild and transition-metal-free method for the α-arylation of aliphatic nitriles with activated heteroaryl halides was developed using NaHMDS or KHMDS as base at ambient temperature. The key to the success of this method is generation of the nitrile anion in the presence of the heteroaryl halide. T...

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Published inJournal of organic chemistry Vol. 70; no. 24; pp. 10186 - 10189
Main Authors Klapars, Artis, Waldman, Jacob H, Campos, Kevin R, Jensen, Mark S, McLaughlin, Mark, Chung, John Y. L, Cvetovich, Raymond J, Chen, Cheng-yi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.11.2005
Amer Chemical Soc
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Abstract A mild and transition-metal-free method for the α-arylation of aliphatic nitriles with activated heteroaryl halides was developed using NaHMDS or KHMDS as base at ambient temperature. The key to the success of this method is generation of the nitrile anion in the presence of the heteroaryl halide. The method is applicable to both primary and secondary carbonitriles and a wide range of heteroaryl halides. Selective monoarylation was observed with primary carbonitriles. The operational simplicity and the mild reaction conditions add to the value of this method as a practical alternative to the preparation of α-heteroaryl carbonitriles.
AbstractList [reaction: see text] A mild and transition-metal-free method for the alpha-arylation of aliphatic nitriles with activated heteroaryl halides was developed using NaHMDS or KHMDS as base at ambient temperature. The key to the success of this method is generation of the nitrile anion in the presence of the heteroaryl halide. The method is applicable to both primary and secondary carbonitriles and a wide range of heteroaryl halides. Selective monoarylation was observed with primary carbonitriles. The operational simplicity and the mild reaction conditions add to the value of this method as a practical alternative to the preparation of alpha-heteroaryl carbonitriles.
A mild and transition-metal-free method for the alpha-arylation of aliphatic nitriles with activated heteroaryl halides was developed using NaHMDS or KHMDS as base at ambient temperature. The key to the success of this method is generation of the nitrile anion in the presence of the heteroaryl halide. The method is applicable to both primary and secondary carbonitriles and a wide range of heteroaryl halides. Selective monoarylation was observed with primary carbonitriles. The operational simplicity and the mild reaction conditions add to the value of this method as a practical alternative to the preparation of alpha-heteroaryl carbonitriles.
A mild and transition-metal-free method for the α-arylation of aliphatic nitriles with activated heteroaryl halides was developed using NaHMDS or KHMDS as base at ambient temperature. The key to the success of this method is generation of the nitrile anion in the presence of the heteroaryl halide. The method is applicable to both primary and secondary carbonitriles and a wide range of heteroaryl halides. Selective monoarylation was observed with primary carbonitriles. The operational simplicity and the mild reaction conditions add to the value of this method as a practical alternative to the preparation of α-heteroaryl carbonitriles.
Author Jensen, Mark S
McLaughlin, Mark
Cvetovich, Raymond J
Waldman, Jacob H
Chen, Cheng-yi
Chung, John Y. L
Klapars, Artis
Campos, Kevin R
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Issue 24
Keywords CARBONYL
CARBANIONS
HALOPYRIDINES
MECHANISM
NUCLEOPHILIC-SUBSTITUTION
Arylation
Sulfur nitrogen heterocycle
Nitrile
Mild operating conditions
Nitrogen heterocycle
Organic halogen compounds
Heterocyclic compound
Oxygen nitrogen heterocycle
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Snippet A mild and transition-metal-free method for the α-arylation of aliphatic nitriles with activated heteroaryl halides was developed using NaHMDS or KHMDS as base...
A mild and transition-metal-free method for the alpha-arylation of aliphatic nitriles with activated heteroaryl halides was developed using NaHMDS or KHMDS as...
[reaction: see text] A mild and transition-metal-free method for the alpha-arylation of aliphatic nitriles with activated heteroaryl halides was developed...
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SubjectTerms Alkylation
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Nitriles - chemical synthesis
Nitriles - chemistry
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Stereoisomerism
Title Mild and Practical Method for the α-Arylation of Nitriles with Heteroaryl Halides
URI http://dx.doi.org/10.1021/jo051737f
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