Site-Selective γ-C(sp3)−H and γ-C(sp2)−H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group

2018 ◽  
Vol 24 (38) ◽  
pp. 9535-9541 ◽  
Author(s):  
Hua Lin ◽  
Chao Wang ◽  
Thomas D. Bannister ◽  
Theodore M. Kamenecka
Keyword(s):  
Free Amino ◽  
Amino Esters ◽  
Directing Group ◽  
Site Selective

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

para-Selective Cyanation of Arenes by H-Bonded Template

2019 ◽  
Author(s):  
Sandeep Pimparkar ◽  
Trisha Bhattacharya ◽  
Arun Maji ◽  
Argha Saha ◽  
Ramasamy Jayarajan ◽  
...  
Keyword(s):  
Selective Functionalization ◽  
Directing Group ◽  
Product Utility ◽  
Site Selective

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work we demonstrate the <i>para</i>-selective introduction of versatile nitrile moiety, enabled by detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools heralds the inception of <i>para</i>-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Metal-free amino-controlled electrochemical intramolecular C–O and C–N couplings by site-selective activation of aryl C–N and C–O bonds

2021 ◽  
Author(s):  
Mu-Jia Luo ◽  
Gui-Fen Lv ◽  
Yang Li ◽  
Jin-Heng Li
Keyword(s):  
Free Amino ◽  
Selective Activation ◽  
Metal Free ◽  
Site Selective

Metal-free amino-assisted electrochemical intramolecular C–O or C–N couplings of amino-2-(2-aminoaryl)phenols are described.

Free Amino Group-Directed γ-C(sp3)–H Arylation of α-Amino Esters with Diaryliodonium Triflates by Palladium Catalysis

2019 ◽  
Vol 84 (9) ◽  
pp. 5684-5694 ◽  
Author(s):  
Pranab K. Pramanick ◽  
Zhibing Zhou ◽  
Zhen-Lin Hou ◽  
Bo Yao
Keyword(s):  
Free Amino ◽  
Palladium Catalysis ◽  
Amino Group ◽  
Amino Esters

scholarly journals A lesson for site-selective C–H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls

2018 ◽  
Vol 9 (1) ◽  
pp. 22-32 ◽  
Author(s):  
Koji Hirano ◽  
Masahiro Miura
Keyword(s):  
Pharmaceutical Chemistry ◽  
Recent Advances ◽  
Directing Group ◽  
Site Selective

This minireview focuses on recent advances in site-selective C–H functionalization on 2-pyridone which is an important heterocyclic motif in medicinal and pharmaceutical chemistry.

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

Ruthenium-catalyzed site-selective C–H arylation of 2-pyridones and 1-isoquinolinones

2017 ◽  
Vol 15 (26) ◽  
pp. 5457-5461 ◽  
Author(s):  
K. Anil Kumar ◽  
Prakash Kannaboina ◽  
Parthasarathi Das
Keyword(s):  
Boronic Acids ◽  
Directing Group ◽  
Site Selective

An efficient Ru(ii)-catalyzed site-selective C–H arylation of 2-pyridones and 1-isoquinolinones with boronic acids by using pyridine as a directing group has been developed.

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