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.

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.

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.

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.

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.

Transition-metal-catalyzed nucleophilic dearomatization of electron-deficient heteroarenes

Synthesis ◽  
2021 ◽  
Author(s):  
Jie Jia ◽  
Fangdong Hu ◽  
Ying Xia
Keyword(s):  
Transition Metal ◽  
Asymmetric Catalysis ◽  
Short Review ◽  
Transition Metal Catalysis ◽  
Powerful Method ◽  
Metal Catalysis ◽  
Unique Method ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Transition-metal-catalyzed nucleophilic dearomatization of electron-deficient heteroarenes, such as pyridines, quinolines, isoquinolines and nitroindoles, has become a powerful method for the access of unsaturated heterocycles in recent decades. This short review summarizes nucleophilic dearomatization of electron-deficient heteroarenes with carbon- and heteroatom-based nucleophiles via transition-metal catalysis. A great number of functionalized heterocycles were obtained in this transformation. Importantly, many of these reactions were carried out in an enantioselective manner by means of asymmetric catalysis, providing a unique method for the construction of enantioenriched heterocycles. 1 Introduction 2 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes via alkynylation 3 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes via arylation 4 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes with other nucleophiles 5 Transition-metal-catalyzed nucleophilic dearomatization with nucleophiles formed in situ 6 Conclusion and outlook

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.

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.

Recent Advance on Benzofuranones: Synthesis and Transformation via C-H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Zhi Tang ◽  
Zhou Tong ◽  
Shuang-Feng Yin ◽  
Nobuaki Kambe ◽  
Renhua Qiu
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Efficient Synthesis ◽  
Bond Functionalization ◽  
Pka Value ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Benzofuranone is a sort of important skeleton in many fields, such as natural products, pharmaceuticals, building blocks, antioxidants and dyes. Their efficient synthesis and transformations have attracted great attentions in organic synthesis. They can be synthesized by Friedel−Crafts reaction, intramolecular dehydration ring-closing reaction and transition-metal-catalyzed reaction, etc. And their direct utilization to prepare other functional molecules enhances their further application. Due to their low pKa value and easy enolization ability, the transformation of benzofuranones via C(3)-H bond functionalization is a hot issue in the last ten years. Herein, we highlight the advances on the synthesis of benzofuranones and its transformation via C-H functionalization. Some of other transformations related to benzofuranones are also referred in this review.

Synthesis of N-Heterocycles via Transition-Metal-Catalyzed Tandem Addition/Cyclization of a Nitrile

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 819-833 ◽  
Author(s):  
Jen-Chieh Hsieh ◽  
Haw-Lih Su
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Nucleophilic Addition ◽  
Radical Addition ◽  
Transition Metal Catalysis ◽  
Late Transition Metal ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Late Transition ◽  
Metal Catalyzed

The diverse methodologies to synthesize N-heterocycles through transition-metal-catalyzed cascade addition/cyclization of a nitrile are discussed in this review. Aspects relating to three types of transition-metal-catalyzed addition of a nitrile with subsequent cyclization include (1) a transition-metal acting as a Lewis acid to accelerate the nucleophilic addition of a nitrile, (2) the late-transition-metal-catalyzed 1,2-insertion of a nitrile, and (3) an in situ generated radical by transition-metal catalysis to implement a radical addition/cyclization tandem reaction. Applications for the synthesis of natural alkaloids, their derivatives, and some bioactive compounds are also summarized herein.1 Introduction2 Nucleophilic Addition of a Nitrile Accelerated by a Lewis Acid2.1 Late-Transition-Metal Catalysis2.2 Early-Transition-Metal Catalysis2.3 Lanthanide-Metal Catalysis2.4 Cyclization from N-Arylnitriliums3 Transition-Metal-Catalyzed Insertion of a Nitrile4 Transition-Metal-Catalyzed Radical Addition of a Nitrile5 Conclusions

Peptide macrocyclization by transition metal catalysis

2020 ◽  
Vol 49 (7) ◽  
pp. 2039-2059 ◽  
Author(s):  
Daniel G. Rivera ◽  
Gerardo M. Ojeda-Carralero ◽  
Leslie Reguera ◽  
Erik V. Van der Eycken
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Conformational Constraints ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Peptide macrocyclization continues expanding with the development of novel transition metal-catalyzed reactions capable of both introducing conformational constraints and generating diversity at the ring-closing moiety.

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