Copper/Silver Cocatalyzed Regioselective C5–H Functionalization of 8-Aminoquinoline Amides with 1,3-Dicarbonyl Compounds

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 1007-1014 ◽  
Author(s):  
Fuxu Zhan ◽  
Wei Zhang ◽  
Huaiqing Zhao
Keyword(s):  
Coupling Reaction ◽  
Catalytic Transformation ◽  
Synthetic Route ◽  
Dicarbonyl Compounds ◽  
Mild Conditions ◽  
Dehydrogenative Coupling

A copper/silver co-catalyzed cross-dehydrogenative coupling reaction is developed to achieve exclusively remote C5–H coupling of 8-aminoquinoline amides with the methylenic sp3 C–H bond of 1,3-dicarbonyl compounds. This protocol provides a highly regioselective synthetic route for the functionalization of 8-aminoquinoline amides at C5 under mild conditions. Preliminary experiments reveal that radicals may be involved in this catalytic transformation.

Copper-catalyzed highly diastereoselective cross-dehydrogenative coupling between 8-hydroxyisochromanes and 1,3-dicarbonyl compounds

2019 ◽  
Vol 6 (13) ◽  
pp. 2275-2279 ◽  
Author(s):  
Zhen Zhang ◽  
Yong-Qiang Tu ◽  
Xiao-Ming Zhang ◽  
Fu-Min Zhang ◽  
Shao-Hua Wang
Keyword(s):  
Coupling Reaction ◽  
Dicarbonyl Compounds ◽  
Dehydrogenative Coupling

A novel copper-catalyzed highly diastereoselective cross-dehydrogenative coupling reaction for the access of tricyclic chromanes from 8-hydroxyisochromanes and 1,3-dicarbonyl compounds.

Copper-Catalyzed Highly Efficient Esterification of Aldehydes with N-Hydroxyphthalimide via Cross-Dehydrogenative Coupling in Water at Room Temperature

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1321-1326 ◽  
Author(s):  
Can Jin ◽  
Weike Su ◽  
Zhicheng Guo ◽  
Xinpeng Jiang ◽  
Jiadi Zhou ◽  
...  
Keyword(s):  
Reaction Time ◽  
Efficient Method ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Short Reaction Time ◽  
Mild Conditions ◽  
Highly Efficient ◽  
Dehydrogenative Coupling ◽  
First Time

A copper-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide and aldehydes using PhI(OAc)2 as an oxidant is described. It is reported for the first time to synthesize NHPI esters in water, providing the corresponding NHPI esters in moderate to good yields. This facile and efficient method is eco-friendly and possesses the advantages of mild conditions, short reaction time, and broad substrate scope.

DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates

Synlett ◽  
2018 ◽  
Vol 30 (01) ◽  
pp. 114-118 ◽  
Author(s):  
Ming-Xing Cheng ◽  
Jing-Wei Lei ◽  
Cai-Xia Xie
Keyword(s):  
Coupling Reaction ◽  
Transition Metal Catalysis ◽  
Secondary Amines ◽  
Metal Catalysis ◽  
New Approach ◽  
Mild Conditions ◽  
Dehydrogenative Coupling ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
Dialkyl Phosphonates

This work reports a DDQ-mediated cross-dehydrogenative-coupling reaction of secondary amines with dialkyl phosphonates under mild conditions. This reaction proceeds efficiently without involving visible light or transition-metal catalysis. This new approach provides efficient access to biologically important α-aminophosphonates.

scholarly journals Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction

RSC Advances ◽  
2021 ◽  
Vol 11 (14) ◽  
pp. 8051-8054
Author(s):  
Rongxiang Chen ◽  
Bing Liu ◽  
Wenbo Li ◽  
Kai-Kai Wang ◽  
Changqing Miao ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Dehydrogenative Coupling ◽  
Aryl Ketones ◽  
High Yields

A cross dehydrogenative coupling reaction of aryl ketones with N-hydroxyphthalimide was realized. The reactions afforded a clean and facile access to diverse N-alkoxyphthalimide derivatives in high yields (up to 99%).

Hydroxymethylation of quinolines via iron promoted oxidative C–H functionalization: synthesis of arsindoline-A and its derivatives

2021 ◽  
Author(s):  
Bangarigalla Shantharjun ◽  
Damera Vani ◽  
Ramanjaneyulu Unnava ◽  
Mummadi Sandeep ◽  
Kallu Rajender Reddy
Keyword(s):  
Coupling Reaction ◽  
Dehydrogenative Coupling

Herein, we report a mild and efficient hydroxymethylation of quinolines via an iron promoted cross-dehydrogenative coupling reaction under external acid free conditions.

scholarly journals Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3223
Author(s):  
Ji-Wei Zhang ◽  
Shao-Hua Xiang ◽  
Shaoyu Li ◽  
Bin Tan
Keyword(s):  
Amino Alcohols ◽  
Sigmatropic Rearrangement ◽  
Synthetic Route ◽  
Mild Conditions ◽  
Good Substrate ◽  
Diaryliodonium Salts ◽  
Axially Chiral

NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.

Topology Selectivity in On-Surface Dehydrogenative Coupling Reaction: Dendritic Structure versus Porous Graphene Nanoribbon

ACS Nano ◽  
2021 ◽  
Vol 15 (3) ◽  
pp. 4617-4626
Author(s):  
Jianmin Huang ◽  
Yu Pan ◽  
Tao Wang ◽  
Shengsheng Cui ◽  
Lin Feng ◽  
...  
Keyword(s):  
Dendritic Structure ◽  
Coupling Reaction ◽  
Graphene Nanoribbon ◽  
Porous Graphene ◽  
Dehydrogenative Coupling ◽  
Structure Versus
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