A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides

Using 2,3-dichloro-5,6-dicyano-p-benzoquinone （DDQ） as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are wel...

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Bibliographic Details
Published inScience China. Chemistry Vol. 58; no. 8; pp. 1323 - 1328
Main Authors Liu, Jie, Zhang, Heng, Yi, Hong, Liu, Chao, Lei, Aiwen
Format Journal Article
LanguageEnglish
Published Beijing Science China Press 01.08.2015
Science Press
Springer Nature B.V
Subjects
Amides
Benzoquinone
Bonding
C-H键
C-N
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Coupling
Functional groups
Oxidizing agents
Physical Sciences
Science & Technology
Sulfonamides
Transition metals
官能团化
氧化偶联
磺胺类药物
苄基
过渡金属催化
酰胺
oxidative coupling
amination
C-N bond formation
C-H functionalization
PALLADIUM
SULFOXIMINES
INTERMOLECULAR AMINATION
PORPHYRINS
COMPLEXES
RUTHENIUM
INSERTIONS
INTRAMOLECULAR AMIDATION
FUNCTIONALIZATION
COPPER-CATALYZED AMIDATION
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Summary:Using 2,3-dichloro-5,6-dicyano-p-benzoquinone （DDQ） as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C-H functionalization and C-N bond formation.
Bibliography:oxidative coupling, C-N bond formation, amination, C-H functionalization
Using 2,3-dichloro-5,6-dicyano-p-benzoquinone （DDQ） as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C-H functionalization and C-N bond formation.
11-5839/O6
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-015-5381-2