O-Acyl oximes: versatile building blocks for N-heterocycle formation in recent transition metal catalysis

2016 ◽  
Vol 14 (5) ◽  
pp. 1519-1530 ◽  
Author(s):  
Huawen Huang ◽  
Jinhui Cai ◽  
Guo-Jun Deng
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Building Blocks ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This review is dedicated to showcase and discuss recent progress on N-heterocycle formation by transition-metal catalyzed annulation from O-acyl oximes.

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 Synthesis of Polyhedral Borane Cluster Fused Heterocycles via Transition Metal Catalyzed B-H Activation

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 391 ◽  
Author(s):  
Ke Cao ◽  
Cai-Yan Zhang ◽  
Tao-Tao Xu ◽  
Ji Wu ◽  
Xin-Yu Wen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Building Blocks ◽  
Bioactive Natural Products ◽  
Fused Heterocycles ◽  
Selective Functionalization ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Photoluminescent Materials ◽  
Borane Cluster

Aromatic heterocycles are ubiquitous building blocks in bioactive natural products, pharmaceutical and agrochemical industries. Accordingly, the carborane-fused heterocycles would be potential candidates in drug discovery, nanomaterials, metallacarboranes, as well as photoluminescent materials. In recent years, the transition metal catalyzed B-H activation has been proved to be an effective protocol for selective functionalization of B-H bond of o-carboranes, which has been further extended for the synthesis of polyhedral borane cluster-fused heterocycles via cascade B-H functionalization/annulation process. This article summarizes the recent progress in construction of polyhedral borane cluster-fused heterocycles via B-H activation.

Recent progress in transition-metal-catalyzed hydrocyanation of nonpolar alkenes and alkynes

2020 ◽  
Vol 18 (3) ◽  
pp. 391-399 ◽  
Author(s):  
Hongru Zhang ◽  
Xin Su ◽  
Kaiwu Dong
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Building Blocks ◽  
Powerful Method ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Hydrocyanation is a powerful method for the preparation of nitriles which are versatile building blocks for the synthesis of amines, acids and amides.

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.

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

5 Metal-Catalyzed C—H Activation

2022 ◽  
Author(s):  
Y.-K. Xing ◽  
P. Fang ◽  
Z.-H. Wang ◽  
T.-S. Mei
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Environmentally Friendly ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Bond Forming ◽  
Organic Electrochemistry ◽  
Metal Catalyzed ◽  
Environmentally Friendly Approach ◽  
Made In

Synthetic organic electrochemistry is currently experiencing a renaissance, the merger of electrochemistry with transition-metal-catalyzed C—H activation would provide not only an environmentally friendly approach, but also offer new opportunities that conventional transition-metal catalysis may not have achieved. In this chapter, we summarize the recent progress made in catalytic C—H activation reactions using organometallic electrochemistry, including C—C, C—O, C—N, C—halogen, and C—P bond-forming reactions.

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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