Enantioselective C–H Functionalization toward Silicon-Stereogenic Silanes

Synthesis ◽  
2022 ◽  
Author(s):  
Chuan He ◽  
Wei Yuan
Keyword(s):  
Transition Metal ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Functionalization ◽  
Recent Advances ◽  
Stereogenic Centers ◽  
Organosilicon Chemistry ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Shed Light

In recent years, transition-metal-catalyzed enantioselective C–H bond functionalization has emerged as a powerful and attractive synthetic approach to access silicon-stereogenic centers, which continues to give impetus for the innovation of chiral organosilicon chemistry. This short review is aimed to summarize recent advances in the construction of silicon-stereogenic silanes via transition-metal-catalyzed enantioselective C–H functionalization. We have endeavored to highlight the great potential of this methodology and hope that this review will shed light on new perspectives, inspire further research in this emerging area.

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.

scholarly journals Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

2014 ◽  
Vol 10 ◽  
pp. 2186-2199 ◽  
Author(s):  
Michael Ghobrial ◽  
Marko D Mihovilovic ◽  
Michael Schnürch
Keyword(s):  
Transition Metal ◽  
Synthetic Approach ◽  
Protecting Group ◽  
Copper Salts ◽  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Synthetic Routes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The synthesis of 1,2,3-trisubstituted indoles was investigated. More specifically, straightforward synthetic routes towards 1-(1,2-diarylindol-3-yl)-N-PG-THIQs (PG = protecting group, THIQ = tetrahydroisoquinoline) employing transition metal-catalyzed C–H and N–H-bond functionalization were explored. It was found that the synthesis of the target compounds is strongly dependent on the order of events. Hence, depending on the requirements of a synthetic problem the most suitable and promising pathway can be chosen. Additionally, a new synthetic approach towards 1,2-diarylindoles starting from 1-arylindole could be established in the course of our investigation by using a palladium-catalyzed protocol. Such 1,2-diarylindoles were successfully reacted with N-Boc-THIQ to furnish 1,2,3-trisubstituted indoles as target compounds. Furthermore, regioselective N-arylation of protected and unprotected 1-(indol-3-yl)-THIQs was successfully conducted using either simple iron or copper salts as catalysts.

Recent Advances in Difluoromethylthiolation

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 197-207 ◽  
Author(s):  
Xuan Xiao ◽  
Zi-Tong Zheng ◽  
Ting Li ◽  
Jing-Lin Zheng ◽  
Ting Tao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Short Review ◽  
Recent Advances ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Sulfur Containing

The difluoromethylthio group (HCF2S), which has been identified as a valuable functionality in drug and agrochemical discovery, has received increased attention recently. Two strategies, difluoromethylation and direct difluoromethylthiolation, have been well established for HCF2S incorporation. The former strategy suffers from the need to prepare sulfur-containing substrates. In contrast, direct difluoromethylthiolation is straightforward and step-economic. This short review covers the recent advances in direct difluoromethylthiolation, including electrophilic, radical, and transition-metal-catalyzed or -promoted reactions­.1 Introduction2 Electrophilic Difluoromethylthiolation3 Radical Difluoromethylthiolation4 Transition-Metal-Catalyzed or -Promoted Difluoromethylthiolation5 Conclusions and Perspectives

Transient- and Native-Directing-Group-Enabled Enantioselective C–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Chuan He ◽  
Bing Zu ◽  
Yonghong Guo ◽  
Jie Ke
Keyword(s):  
Carboxylic Acid ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Functionalization ◽  
Axial Chirality ◽  
Planar Chirality ◽  
Directing Group ◽  
Metal Catalyzed

AbstractIn recent years, transition-metal-catalyzed enantioselective C–H bond functionalization using chiral transient directing groups (cTDGs) or native directing groups (NDGs) has emerged as a powerful and attractive­ synthetic approach to streamline the synthesis of chiral molecules­. This short review focuses on recent advances on imine-based cTDGs strategies and native amine and carboxylic acid directed strategies for the asymmetric functionalization of various C–H bonds. We have endeavored to highlight the great potential of this methodology and hope that this review will inspire further research in this area.1 Introduction2 Transient-Directing-Group-Enabled Enantioselective C–H Functionalization2.1 Generation of Central Chirality2.2 Generation of Axial Chirality2.3 Generation of Planar Chirality3 Native-Directing-Group-Enabled Enantioselective C–H Functionalization3.1 Native Amines as Directing Groups3.2 Native Carboxylic Acids as Directing Groups4 Conclusions and Outlook

The Transient Directing Group Strategy: A New Trend in Transition-Metal-Catalyzed C–H Bond Functionalization

Synthesis ◽  
2017 ◽  
Vol 49 (21) ◽  
pp. 4808-4826 ◽  
Author(s):  
Tatiana Besset ◽  
Qun Zhao ◽  
Thomas Poisson ◽  
Xavier Pannecoucke
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Short Review ◽  
Point Of View ◽  
Bond Functionalization ◽  
Carbonyl Derivatives ◽  
Direct Functionalization ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

In recent years, the C–H bond activation field has known very fast expansion offering valuable synthetic tools. Consequently, the quest for new approaches to afford atom- and step-economical processes has driven the scientific community to imagine original strategies. In this context, the direct functionalization of substrates by a transition-metal-catalyzed C–H bond activation using a transient directing group has emerged as a promising approach. This short review focuses on the major progress made in this field to provide to the reader an overview of the recent advances.1 Introduction2 From a Historical Point of View3 Functionalization of Carbonyl Derivatives4 Functionalization of Amines Derivatives5 Summary and Outlook

Recent Advances in Transition-Metal-Catalyzed C–H Addition to Nitriles

Synthesis ◽  
2021 ◽  
Author(s):  
Wei-Wei Liao ◽  
Shu-Qiang Cui
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Recent Progress ◽  
Building Blocks ◽  
Short Review ◽  
Synthetic Approach ◽  
Bond Forming ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed C–H bond addition to nitriles has emerged as a powerful synthetic approach for the construction of C–C bonds in organic synthesis. Due to the merits of atom- and step-economy, as well the easy availability of the starting materials, these transformations not only deliver acyclic aryl ketone products with nitriles­ as C-building blocks, but can also be utilized for the highly efficient­ assembly of azaheterocyclic skeletons using nitriles as C–N building blocks. This short review summarizes recent progress on transition-metal-catalyzed C–C bond-forming reactions based on C(sp2)–H and C(sp3)–H additions to nitriles.1 Introduction2 Palladium-Catalyzed C–H Addition to Nitriles2.1 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Ketone (Imine) Products2.2 Palladium-Catalyzed C–H Addition to Nitriles for the Preparation of Azaheterocycles2.3 Palladium-Catalyzed C–H Addition to Nitriles/1,2-Rearangement3 Other Transition-Metal-Catalyzed C–H Additions to Nitriles4 Summary and Outlook

scholarly journals Recent advances in transition metal-catalyzed C–H bond functionalization of ferrocene derivatives

2015 ◽  
Vol 44 (22) ◽  
pp. 10128-10135 ◽  
Author(s):  
Luis A. López ◽  
Enol López
Keyword(s):  
Transition Metal ◽  
Ferrocene Derivatives ◽  
Bond Functionalization ◽  
Recent Advances ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

In this Perspective, recent advances in the emerging field of transition metal-catalyzed C–H bond functionalization of ferrocene derivatives are summarized.

Chelation-assisted transition metal-catalysed C–H chalcogenylations

2020 ◽  
Vol 7 (8) ◽  
pp. 1022-1060 ◽  
Author(s):  
Wenbo Ma ◽  
Nikolaos Kaplaneris ◽  
Xinyue Fang ◽  
Linghui Gu ◽  
Ruhuai Mei ◽  
...  
Keyword(s):  
Transition Metal ◽  
Recent Advances ◽  
Site Selectivity ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This review summarizes recent advances in C–S and C–Se formations via transition metal-catalyzed C–H functionalization utilizing directing groups to control the site-selectivity.

Hydroxylamines as One-Atom Nitrogen Sources for Metal-Catalyzed Cycloadditions

Synthesis ◽  
2021 ◽  
Author(s):  
Xinjun Luan ◽  
Jingxun Yu
Keyword(s):  
Transition Metal ◽  
Nitrogen Source ◽  
Nucleophilic Reagent ◽  
Nitrogen Sources ◽  
Short Review ◽  
Indole Derivatives ◽  
Electrophilic Amination ◽  
Intramolecular Cycloaddition ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed C–N bond formation is one of the most important pathways to synthesize N-heterocycles. Hydroxylamines can be transformed into a nucleophilic reagent to react with a carbon cation or coordinate with a transition metal; it can also become an electrophilic nitrogen source to react with arenes, alkenes, and alkynes. In this short review, the progress made on transition-metal-catalyzed cycloadditions with hydroxylamines as a nitrogen source is summarized.1 Introduction2 Cycloaddition To Form Aziridine Derivatives2.1 Intramolecular Cycloaddition To Form Aziridine Derivatives2.2 Intermolecular Cycloaddition To Form Aziridine Derivatives3 Cycloaddition To Form Indole Derivatives4 Cycloaddition To Form Other N-Heterocycles4.1 Aza-Heck-Type Amination Reactions4.2 Nitrene Insertion Amination Reactions4.3 Intramolecular Nucleophilic and Electrophilic Amination Reactions5 Conclusion and Outlook

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