Metal-Free Aerobic Oxidative Cyanation of Tertiary Amines: Azobis(isobutyronitrile) (AIBN) as a Sole Cyanide Source

An aerobic oxidative cyanation for the synthesis of α-aminonitriles was reported. The formation of C­(sp3)-CN bonds was achieved under a metal-free condition by utilizing azobis­(isobutyronitrile) as a sole organic cyanide source with the combination of pivalic acid and sodium acetate as additives....

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Published inJournal of organic chemistry Vol. 82; no. 23; pp. 12786 - 12790
Main Authors Liu, Peng-Yu, Zhang, Chao, Zhao, Shi-Chen, Yu, Fang, Li, Fei, He, Yu-Peng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.12.2017
Amer Chemical Soc
Subjects
additives
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
cyanides
organic chemistry
Physical Sciences
Science & Technology
sodium acetate
tertiary amines
H BOND ACTIVATION
COUPLING REACTIONS
NITRILES
SODIUM-CYANIDE
HYDROGEN-PEROXIDE
AZOBISISOBUTYRONITRILE
COPPER-CATALYZED CYANATION
STRECKER REACTION
HIGHLY EFFICIENT
ALPHA-CYANATION
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Summary:An aerobic oxidative cyanation for the synthesis of α-aminonitriles was reported. The formation of C­(sp3)-CN bonds was achieved under a metal-free condition by utilizing azobis­(isobutyronitrile) as a sole organic cyanide source with the combination of pivalic acid and sodium acetate as additives.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.7b02021