scholarly journals Regioselective Functionalization of Quinolines through C-H Activation: A Comprehensive Review

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5467
Author(s):  
Alessandra Corio ◽  
Christine Gravier-Pelletier ◽  
Patricia Busca
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Green Chemistry ◽  
Transition Metal Catalysis ◽  
Synthetic Methods ◽  
Metal Catalysis ◽  
Comprehensive Review ◽  
Metal Catalyzed ◽  
Regioselective Functionalization ◽  
Site Selective

Quinoline is a versatile heterocycle that is part of numerous natural products and countless drugs. During the last decades, this scaffold also became widely used as ligand in organometallic catalysis. Therefore, access to functionalized quinolines is of great importance and continuous efforts have been made to develop efficient and regioselective synthetic methods. In this regard, C-H functionalization through transition metal catalysis, which is nowadays the Graal of organic green chemistry, represents the most attractive strategy. We aim herein at providing a comprehensive review of methods that allow site-selective metal-catalyzed C-H functionalization of quinolines, or their quinoline N-oxides counterparts, with a specific focus on their scope and limitations, as well as mechanistic aspects if that accounts for the selectivity.

The C–H functionalization of N-alkoxycarbamoyl indoles by transition metal catalysis

2021 ◽  
Vol 19 (37) ◽  
pp. 7949-7969
Author(s):  
Prasanjit Ghosh ◽  
Sajal Das
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Indole and its congeners are ubiquitous nitrogen containing organic scaffolds found in a plethora of natural products. This review aims to highlight the transition-metal catalyzed C–H functionalization of N-alkoxycarbamoyl indoles.

Transition Metal-Catalyzed Enantioselective α-Arylation of Carbonyl Compounds to Give Tertiary Stereocenters

Synthesis ◽  
2021 ◽  
Author(s):  
Manuel Orlandi ◽  
Margarita Escudero-Casao ◽  
Giulia Licini
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Carbonyl Group ◽  
Carbonyl Compounds ◽  
Short Review ◽  
Transition Metal Catalysis ◽  
Biologically Active ◽  
Metal Catalysis ◽  
Quaternary Stereocenters ◽  
Metal Catalyzed

Enantioenriched α-aryl carbonyl compounds are ubiquitous in natural products and biologically active compounds. Their synthesis has been explored over the last few decades and several methods now exist that allow for the enantioselective formation of a C(sp3)-C(sp2) bond in α-position to a carbonyl group. However, although the formation of quaternary stereocenters has been fairly well established, the enantioselective formation of tertiary stereocenters proved more challenging due to facile product post-reaction racemization. In this short review, we summarize the methods reported so far for the asymmetric α-arylation of enolates and analogues that rely on transition metal catalysis.

C–H functionalization of quinazolinones by transition metal catalysis

2020 ◽  
Vol 18 (24) ◽  
pp. 4497-4518 ◽  
Author(s):  
Prasanjit Ghosh ◽  
Bhaskar Ganguly ◽  
Sajal Das
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Important Class ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Quinazolinone and its derivatives are an important class of heterocyclic scaffolds in pharmaceuticals and natural products. This review provides the recent research advances in the transition metal catalyzed selective C–H bond functionalization of quinazolinone.

Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

2017 ◽  
Vol 4 (10) ◽  
pp. 1981-1986 ◽  
Author(s):  
Huijie Qiao ◽  
Suyan Sun ◽  
Yue Zhang ◽  
Hongmei Zhu ◽  
Xiaomeng Yu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Photoredox Catalysis ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Site Selective

A simple and efficient protocol for the transition metal-catalyzed site-selective C–H phosphonation of 8-aminoquinoline at the C4 or C5 positions via a photoredox process was developed.

Recent development of synthetic preparation methods for guanidines via transition metal catalysis

2015 ◽  
Vol 51 (2) ◽  
pp. 254-265 ◽  
Author(s):  
Wen-Xiong Zhang ◽  
Ling Xu ◽  
Zhenfeng Xi
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Preparation Methods ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

This article provides an overview of guanidine synthesis via transition-metal-catalyzed reactions including cycloaddition, guanylation and tandem guanylation/cyclization.

scholarly journals Recent Developments in Transition-Metal Catalyzed Direct C–H Alkenylation, Alkylation, and Alkynylation of Azoles

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4970
Author(s):  
Su Chen ◽  
Prabhat Ranjan ◽  
Leonid G. Voskressensky ◽  
Erik V. Van der Eycken ◽  
Upendra K. Sharma
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Significant Progress ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Recent Advances ◽  
Regioselective Alkylation ◽  
Recent Developments ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The transition metal-catalyzed C–H bond functionalization of azoles has emerged as one of the most important strategies to decorate these biologically important scaffolds. Despite significant progress in the C–H functionalization of various heteroarenes, the regioselective alkylation and alkenylation of azoles are still arduous transformations in many cases. This review covers recent advances in the direct C–H alkenylation, alkylation and alkynylation of azoles utilizing transition metal-catalysis. Moreover, the limitations of different strategies, chemoselectivity and regioselectivity issues will be discussed in this review.

Transition metal-catalyzed direct nucleophilic addition of C–H bonds to carbon–heteroatom double bonds

2014 ◽  
Vol 5 (6) ◽  
pp. 2146-2159 ◽  
Author(s):  
Xi-Sha Zhang ◽  
Kang Chen ◽  
Zhang-Jie Shi
Keyword(s):  
Transition Metal ◽  
Nucleophilic Addition ◽  
Transition Metal Catalysis ◽  
Grignard Reaction ◽  
Double Bonds ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Compared with the traditional Grignard reaction, direct insertion of polar double bonds to C–H bonds via transition-metal catalysis is ideal from the viewpoint of atom-, step- and cost-economy and the avoidance of the waste emission, as well as of the complex manipulation of sensitive reagents.

Organocatalytic Atom-Transfer C(sp3)–H Oxidation

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2331-2336 ◽  
Author(s):  
Michael Hilinski ◽  
Shea Johnson ◽  
Logan Combee
Keyword(s):  
Transition Metal ◽  
Late Stage ◽  
Transition Metal Catalysis ◽  
Great Promise ◽  
Atom Transfer ◽  
Complex Molecules ◽  
Metal Catalysis ◽  
Iminium Salt ◽  
Site Selective

Predictably site-selective catalytic methods for intermolecular C(sp3)–H hydroxylation and amination hold great promise for the synthesis and late-stage modification of complex molecules. Transition-metal catalysis has been the most common approach for early investigations of this type of reaction. In comparison, there are far fewer ­reports of organocatalytic methods for direct oxygen or nitrogen insertion into C–H bonds. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of an iminium salt that catalyzes both oxygen and nitrogen insertion.1 Introduction2 Background: C–H Oxidation Capabilities of Heterocyclic Oxidants3 Oxaziridine-Mediated Catalytic Hydroxylation4 Dioxirane-Mediated Catalytic Hydroxylation5 Iminium Salt Catalysis of Hydroxylation and Amination6 Conclusion and Outlook

Sign in / Sign up

Export Citation Format

Share Document