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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Abstract 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.
AbstractList 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.
An aerobic oxidative cyanation for the synthesis of α-aminonitriles was reported. The formation of C(sp )-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.
An aerobic oxidative cyanation for the synthesis of alpha-aminonitriles was reported. The formation of C(sp(3))-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.
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.
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.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.
Author He, Yu-Peng
Liu, Peng-Yu
Li, Fei
Zhang, Chao
Zhao, Shi-Chen
Yu, Fang
AuthorAffiliation College of Chemistry, Chemical Engineering and Environmental Engineering
AuthorAffiliation_xml – name: College of Chemistry, Chemical Engineering and Environmental Engineering
Author_xml – sequence: 1
  givenname: Peng-Yu
  surname: Liu
  fullname: Liu, Peng-Yu
– sequence: 2
  givenname: Chao
  surname: Zhang
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  givenname: Shi-Chen
  surname: Zhao
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  fullname: Yu, Fang
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  orcidid: 0000-0002-0676-6627
  surname: He
  fullname: He, Yu-Peng
  email: yupeng.he@lnpu.edu.cn
BackLink https://www.ncbi.nlm.nih.gov/pubmed/29110484$$D View this record in MEDLINE/PubMed
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Keywords H BOND ACTIVATION
COUPLING REACTIONS
NITRILES
SODIUM-CYANIDE
HYDROGEN-PEROXIDE
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COPPER-CATALYZED CYANATION
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Snippet 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...
An aerobic oxidative cyanation for the synthesis of alpha-aminonitriles was reported. The formation of C(sp(3))-CN bonds was achieved under a metal-free...
An aerobic oxidative cyanation for the synthesis of α-aminonitriles was reported. The formation of C(sp )-CN bonds was achieved under a metal-free condition by...
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...
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...
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SubjectTerms additives
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
cyanides
organic chemistry
Physical Sciences
Science & Technology
sodium acetate
tertiary amines
Title Metal-Free Aerobic Oxidative Cyanation of Tertiary Amines: Azobis(isobutyronitrile) (AIBN) as a Sole Cyanide Source
URI http://dx.doi.org/10.1021/acs.joc.7b02021
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https://www.ncbi.nlm.nih.gov/pubmed/29110484
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Volume 82
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