Palladium-Catalyzed Highly Selective ortho-Halogenation (I, Br, Cl) of Arylnitriles via sp2 C–H Bond Activation Using Cyano as Directing Group

2013 ◽  
Vol 78 (6) ◽  
pp. 2786-2791 ◽  
Author(s):  
Bingnan Du ◽  
Xiaoqing Jiang ◽  
Peipei Sun
Keyword(s):  
Bond Activation ◽  
Palladium Catalyzed ◽  
Directing Group

Carbon Dioxide-Driven Palladium-Catalyzed C–H Activation of Amines: A Unified Approach for the Arylation of Aliphatic and Aromatic Primary and Secondary Amines

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 519-524 ◽  
Author(s):  
Michael Young ◽  
Mohit Kapoor ◽  
Pratibha Chand-Thakuri ◽  
Justin Maxwell ◽  
Daniel Liu ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Bond Activation ◽  
Secondary Amines ◽  
Activation Process ◽  
Unified Approach ◽  
Benzylic Amines ◽  
Palladium Catalyzed ◽  
Group A ◽  
Directing Group ◽  
Site Selective

Amines are an important class of compounds in organic chemistry and serve as an important motif in various industries, including pharmaceuticals, agrochemicals, and biotechnology. Several methods have been developed for the C–H functionalization of amines using various directing groups, but functionalization of free amines remains a challenge. Here, we discuss our recently developed carbon dioxide driven highly site-selective γ-arylation of alkyl- and benzylic amines via a palladium-catalyzed C–H bond-activation process. By using carbon dioxide as an inexpensive, sustainable, and transient directing group, a wide variety of amines were arylated at either γ-sp3 or sp2 carbon–hydrogen bonds with high selectivity based on substrate and conditions. This newly developed strategy provides straightforward access to important scaffolds in organic and medicinal chemistry without the need for any expensive directing groups.1 Introduction2 C(sp3)–H Arylation of Aliphatic Amines3 C(sp2)–H Arylation of Benzylamines4 Mechanistic Questions5 Future Outlook

Synthesis of Biphenyl-2-carbonitrile Derivatives via a Palladium-Catalyzed sp2C−H Bond Activation Using Cyano as a Directing Group

2011 ◽  
Vol 13 (6) ◽  
pp. 1286-1289 ◽  
Author(s):  
Wu Li ◽  
Zhipeng Xu ◽  
Peipei Sun ◽  
Xiaoqing Jiang ◽  
Min Fang
Keyword(s):  
Bond Activation ◽  
Palladium Catalyzed ◽  
Directing Group

Mechanistic Investigation of Palladium-Catalyzed meta-C–H Bond Activation of Arenes with a Carboxyl Directing Group

2021 ◽  
Vol 86 (19) ◽  
pp. 13475-13480
Author(s):  
Huiling Li ◽  
Miao Yang ◽  
Liyuan Jin ◽  
Yun-Fang Yang ◽  
Yuan-Bin She
Keyword(s):  
Bond Activation ◽  
Mechanistic Investigation ◽  
Palladium Catalyzed ◽  
Directing Group

Selective Diacetoxylation of Disubstituted 1,2,3-Triazoles through Palladium-Catalyzed C–H Activation

Synlett ◽  
2018 ◽  
Vol 29 (10) ◽  
pp. 1373-1378 ◽  
Author(s):  
Huiling Cheng ◽  
Yubo Jiang ◽  
Jianhua Yang ◽  
Fen Zhao ◽  
Yaowen Liu ◽  
...  
Keyword(s):  
High Selectivity ◽  
Bond Activation ◽  
Triazole Ring ◽  
Palladium Catalyzed ◽  
Group A ◽  
Directing Group

A simple and efficient selective diacetoxylation of 1,4-disubstituted 1,2,3-triazoles by Pd-catalyzed C–H bond activation is described. PhI(OAc)2 was used as an acetyloxy source to convert aromatic sp2 C–H bonds into C–O bonds with high selectivity by employing a 1,2,3-triazole ring as an elegant directing group. A range of 1,2,3-triazoles bearing two acetyloxy groups can be readily synthesized by the reaction.

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