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

Transition-Metal-Catalyzed Enantioselective Synthesis of Indoles from 2-Alkynylanilines

Synthesis ◽  
2022 ◽  
Author(s):  
Zhi-Shi Ye ◽  
Jin-cheng Li ◽  
Gang Wang
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Short Review ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Indole Derivatives ◽  
Cross Coupling Reaction ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Optically active indole derivatives are ubiquitous in natural products and widely recognized as privileged components in pharmacologically relevant compounds. Therefore, developing catalytic asymmetric approaches for constructing indole derivatives is highly desirable. In this short review, transition-metal-catalyzed enantioselective synthesis of indoles from 2-alkynylanilines is summarized. 1 Introduction 2 Aminometalation triggered asymmetric cross-coupling reaction/insertion 2.1 Asymmetric Cross-Coupling Reaction 2.2 Asymmetric insertion of C=O, C=C and C≡N bonds 3 Asymmetric relay catalysis 4 Conclusion

Chromium-Catalyzed Cross-Couplings and Related Reactions

Synthesis ◽  
2019 ◽  
Vol 51 (10) ◽  
pp. 2100-2106 ◽  
Author(s):  
Jie Li ◽  
Paul Knochel
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Short Review ◽  
High Price ◽  
Nickel Catalysis ◽  
Catalytic Reactivity ◽  
Transition Metal Catalyzed ◽  
Low Valent ◽  
Metal Catalyzed ◽  
Remarkable Progress

Transition-metal-catalyzed cross-couplings have been recognized as a powerful tool for sustainable syntheses. Despite the fact that remarkable progress was achieved by palladium and nickel catalysis, the high price and toxicity still remained a drawback. Recently, naturally more abundant and less toxic low-valent chromium salts, such as Cr(II) and Cr(III) chlorides, displayed notable unique catalytic reactivity. Thus, recent progress in the field of chromium-catalyzed cross-couplings and related reactions are highlighted in the present short review until December­ 2018.1 Introduction and Early Chromium-Mediated Reactions2 Chromium-Catalyzed Cross-Couplings and Related Reactions3 Conclusion

scholarly journals On the water structure at hydrophobic interfaces and the roles of water on transition-metal catalyzed reactions: A short review

2017 ◽  
Vol 285 ◽  
pp. 57-64 ◽  
Author(s):  
Xiaohong Zhang ◽  
Torrie E. Sewell ◽  
Brittany Glatz ◽  
Sapna Sarupria ◽  
Rachel B. Getman
Keyword(s):  
Transition Metal ◽  
Water Structure ◽  
Short Review ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

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 stereo- and regioselective hydrosilylation of unsymmetrical alkynes

Synthesis ◽  
2021 ◽  
Author(s):  
Peng He ◽  
Meng-Yang Hu ◽  
Xin-Yu Zhang ◽  
Shou-Fei Zhu
Keyword(s):  
Transition Metal ◽  
Short Review ◽  
Different Types ◽  
Transition Metal Catalyzed ◽  
Alkyne Hydrosilylation ◽  
Metal Catalyzed

The alkyne hydrosilylation is one of the most efficient methods for the synthesis of alkenylsilicons and has been a hot topic of research for decades. This short review summarizes the progress of transition-metal-catalyzed stereo- and regioselective hydrosilylation of unsymmetrical alkynes. Topics are discussed based on different types of alkynes and the selectivities.

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

Transition-Metal-Catalyzed Annulative Coupling Cascade for the Synthesis of 3-Methyleneisoindolin-1-ones

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 807-818 ◽  
Author(s):  
So Won Youn
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Short Review ◽  
Coupling Reactions ◽  
Cyclization Reactions ◽  
One Pot ◽  
Bond Forming ◽  
Wide Range ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This short review describes the recent progress made on transition-metal-catalyzed annulative couplings for the synthesis of 3-methyleneisoindolin-1-ones, which are useful intermediates for the synthesis of numerous alkaloids and can be often found in a wide range of natural products and pharmaceuticals. In particular, new one-pot multiple C–C/C–N bond-forming processes for the construction of the 5-methylenepyrrol-2-one nucleus of such compounds are summarized.1 Introduction2 Intramolecular Cyclization Reactions: C3–N or C3–C3a and C–C Bond Formation3 Intermolecular Annulative Coupling Reactions3.1 C3–C3a and C3–N Bond Formation3.2 C1–C7a and C3–N Bond Formation3.3 C1–C7a and C1–N Bond Formation3.4 C1–C7a, C1–N and C3–N Bond Formation3.5 C3–C3a, C1–C7a, C1–N and C3–N Bond Formation: A Pd-Catalyzed One-Pot Sonogashira Coupling–Carbonylation–Amination–Cyclization Cascade4 Conclusion

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