Palladium-Catalyzed Arylation of Cyclopropanes via Directing Group-Mediated C(sp3)–H Bond Activation To Construct Quaternary Carbon Centers: Synthesis of cis- and trans-1,1,2-Trisubstituted Chiral Cyclopropanes

2013 ◽  
Vol 15 (24) ◽  
pp. 6202-6205 ◽  
Author(s):  
Naoyuki Hoshiya ◽  
Takaaki Kobayashi ◽  
Mitsuhiro Arisawa ◽  
Satoshi Shuto
Keyword(s):  
Bond Activation ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Cis And Trans

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

scholarly journals Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds

2018 ◽  
Author(s):  
Vincent van der Puyl ◽  
Joseph Derosa ◽  
Keary Engle
Keyword(s):  
Amino Acid ◽  
Tertiary Amine ◽  
Carbonyl Compounds ◽  
Amino Acid Derivatives ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Two Component ◽  
Directing Group

We report a regioselective, nickel-catalyzed <i>syn</i>-1,2-carboamination of non-conjugated alkenyl carbonyl compounds with <i>O</i>-benzoyl hydroxylamine (N–O) electrophiles and aryl/alkylzinc nucleophiles to afford β- and γ-amino acid derivatives. This method enables preparation of products containing structurally diverse tertiary amine motifs, including heterocycles, and can also be used to form quaternary carbon centers. The reaction takes advantage of a tethered 8-aminoquinoline directing group to control the regiochemical outcome and suppress two-component coupling between the N–O electrophile and organozinc nucleophile.

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
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