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.

scholarly journals Site-Selective Ruthenium-Catalyzed C–H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group

2019 ◽  
Vol 84 (20) ◽  
pp. 12893-12903 ◽  
Author(s):  
Yu-Chao Yuan ◽  
Christian Bruneau ◽  
Thierry Roisnel ◽  
Rafael Gramage-Doria
Keyword(s):  
Boronic Acids ◽  
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

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

scholarly journals External oxidant-compatible phosphorus(III)-directed site-selective C–H carbonylation

2020 ◽  
Vol 6 (51) ◽  
pp. eabd1378
Author(s):  
Ben Dong ◽  
Jiasheng Qian ◽  
Mingjie Li ◽  
Zheng-Jun Wang ◽  
Minyan Wang ◽  
...  
Keyword(s):  
Palladium Catalysis ◽  
High Reactivity ◽  
X Ray ◽  
Compatible System ◽  
Directing Group ◽  
Positional Selectivity ◽  
Site Selective ◽  
Selection Of

The first development of an external oxidant-compatible system involving a phosphorus(III)-directed C–H functionalization has been uncovered. An efficient C–H esterification of indoles with CO and alcohols has been reported in which the high reactivity and the exclusive C7-selectivity derives from the selection of a P(III)–directing group and the utilization of benzoquinone as an external oxidant with palladium catalysis. This strategy shows many advantages, involving an easily accessible and removable directing group, the use of cheap carbonylation sources, a broad substrate scope, and excellent positional selectivity. Two cyclopalladated intermediates were confirmed by x-ray analysis, uncovering key mechanistic features of this P(III)-directed C–H metalation event.

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