Cyanomethylation of the Benzene Rings and Pyridine Rings via Direct Oxidative Cross-Dehydrogenative Coupling with Acetonitrile

A novel and efficient approach for the amine-directed dehydrogenative C­(sp2)–C­(sp3) coupling of arylamines with acetonitrile was reported by using FeCl2 as the catalyst. Substituted anilines, aminopyridines, naphthylamines, and some nitrogen-containing heterocyclic arylamines react with inactive a...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 10; pp. 2030 - 2034
Main Authors Yao, Hua, Zhong, Xiaoyang, Wang, Bingqing, Lin, Sen, Yan, Zhaohua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.03.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM-CATALYZED CYANATION
ALPHA-ARYLATION
ARYL HALIDES
AMIDES
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Summary:A novel and efficient approach for the amine-directed dehydrogenative C­(sp2)–C­(sp3) coupling of arylamines with acetonitrile was reported by using FeCl2 as the catalyst. Substituted anilines, aminopyridines, naphthylamines, and some nitrogen-containing heterocyclic arylamines react with inactive acetonitrile to form the corresponding arylacetonitriles in moderate to good yields. This protocol features nontoxic iron catalysis, efficient atom economy, nonprefunctionalized starting materials, good regioselectivity, and excellent compatibility of functional groups and aromatic rings, providing a novel, straightforward, and green approach toward arylacetonitriles.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00498