Recent Developments in Highly Stereoselective Michael Addition Reactions Catalyzed by Metal Complexes

Synthesis ◽  
2020 ◽  
Vol 52 (06) ◽  
pp. 781-795 ◽  
Author(s):  
Alexander N. Reznikov ◽  
Yuri N. Klimochkin
Keyword(s):  
Transition Metal ◽  
Michael Addition ◽  
Rapid Development ◽  
Short Review ◽  
Cascade Reactions ◽  
Addition Reactions ◽  
Asymmetric Catalytic ◽  
Michael Reactions ◽  
Recent Developments ◽  
Metal Catalyzed

Achieving high enantioselectivity and diastereoselectivity simultaneously­ is a rather challenging task for asymmetric catalytic synthesis­. Thanks to the rapid development of asymmetric transition-metal catalysis, significant progress has been made during recent years in achieving highly enantio- and diastereoselective conjugate addition reactions with a diverse combination of Michael donors and acceptors. This short review surveys the advances in transition-metal-catalyzed asymmetric diastereoselective Michael addition including diastereodivergent catalysis developed between 2015 and 2019. The review is divided into multiple parts according to the type of nucleophiles involved in the reaction.1 Introduction2 Addition of Functionalized Ketones and Dicarbonyl Compounds3 Addition of Aldimino Esters and Their Cyclic Analogues4 Addition of Indolin-2-ones5 Vinylogous Michael Reactions6 Other Michael Donors7 Cascade Reactions Initiated by Michael Addition8 Conclusion

Recent Developments in Photochemical and Electrochemical Decarboxylative C(sp3)–N Bond Formation

Synthesis ◽  
2020 ◽  
Vol 52 (09) ◽  
pp. 1357-1368 ◽  
Author(s):  
Lifang Tian ◽  
Yahui Wang ◽  
Yue Zheng ◽  
Xiaoqing Shao ◽  
Velayudham Ramadoss
Keyword(s):  
Rapid Development ◽  
Bond Formation ◽  
Short Review ◽  
Toxic Substances ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Drug Molecules ◽  
Recent Developments ◽  
Metal Catalyzed ◽  
Nitrogen Containing Compounds

Considering the important applications of nitrogen-containing compounds in agrochemical materials and biomolecular drug molecules, research on methods for the construction of C–N bonds quickly and efficiently has become an important topic in synthetic chemistry. Carboxylic acids are inexpensive, stable, and non-toxic substances that are widely present in Nature, which makes them appealing as potential coupling partners for C(sp3)–N bond-forming reactions. Moreover, compared with the well-established transition-metal-catalyzed protocols, the rapid development of photoredox catalysis and electrochemical methods in recent years provides options for chemists to design new synthetic routes. In this short review, we concentrate on the decarboxylative C(sp3)–N coupling reactions mediated by visible light or electricity, with special attention on mechanistic insights.1 Introduction2 Photoredox-Mediated Decarboxylative C(sp3)–N Bond Formation2.1 Intramolecular Decarboxylation2.2 Intermolecular Decarboxylation3 Electrochemistry-Induced Decarboxylative C(sp3)–N Bond Formation3.1 Intramolecular Decarboxylation3.2 Intermolecular Decarboxylation4 Conclusions and Outlook

Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3215-3223 ◽  
Author(s):  
Yi-Hung Chen ◽  
Mario Ellwart ◽  
Vladimir Malakhov ◽  
Paul Knochel
Keyword(s):  
Transition Metal ◽  
Short Review ◽  
Metal Catalyst ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Organic Halides ◽  
Bond Forming Reactions ◽  
Recent Developments ◽  
Metal Catalyzed ◽  
General Aspects

Organozinc species are powerful reagents for performing carbon–carbon and carbon–heteroatom bond-forming reactions in the presence of a transition-metal catalyst. However, extended applications of zinc reagents have been hampered by their moderate air- and moisture­-stability. This short review presents our recent developments on the preparation of solid aryl, benzyl, heteroaryl, allyl zinc pivalates and zinc amide enolate reagents with greatly enhanced stability toward to air and moisture.1 Introduction2 Preparation of Organozinc Pivalates2.1 Using Organic Halides as Substrates2.2 Using a Directed Metalation on Functionalized Arenes and Heteroarenes2.3 Preparation of Solid Allylic Zinc Pivalates3 General Reactivity Patterns of Organozinc Pivalates3.1 General Aspects3.2 Transition-Metal-Catalyzed Cross-Couplings3.3 Other Carbon–Carbon Bond-Forming Reactions Using Organozinc Pivalates3.4 Preparation and Reactions of Solid, Salt-Stabilized Zinc Amide Enolates as New, Convenient Reformatsky Reagents4 Conclusion

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

Reactions of secondary propargylamines with heteroallenes for the synthesis of diverse heterocycles

2018 ◽  
Vol 47 (11) ◽  
pp. 3861-3898 ◽  
Author(s):  
Vsevolod A. Peshkov ◽  
Olga P. Pereshivko ◽  
Anton A. Nechaev ◽  
Anatoly A. Peshkov ◽  
Erik V. Van der Eycken
Keyword(s):  
Transition Metal ◽  
Recent Developments ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This focused review aims to summarize recent developments in the processes involving additions of secondary propargylamines to various heteroallenes and subsequent transition metal-catalyzed or electrophile-mediated cyclizations.

Amide-Directed Reactions of Small Carbocycles

2021 ◽  
Vol 25 ◽  
Author(s):  
Pavel M. Yamanushkin ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Nucleophilic Addition ◽  
Addition Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: The topic of this review is the amide-directed functionalization of strained carbocycles — specifically, unsaturated or saturated three- and four-membered rings. The following approaches are discussed: a) directed carbometallation and hydrometallation of cyclopropenes catalyzed by transition metals; b) directed metal-templated nucleophilic addition reactions; c) directed C-H functionalization, including transition metal-catalyzed C-H-activation reactions; and d) directed radical additions.

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Synthesis ◽  
2021 ◽  
Author(s):  
Leonid Fershtat ◽  
Fedor Teslenko
Keyword(s):  
Transition Metal ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
State Of The Art ◽  
Short Review ◽  
Advanced Materials ◽  
Metal Free ◽  
Recent Advances ◽  
Application Potential ◽  
Metal Catalyzed

Five-membered heterocyclic N-oxides attracted special attention due to their strong application potential in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are constantly required. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are briefly summarized. Main routes to transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. Transformation patterns of the hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.

Recent Developments in C–C Bond Formation Using Catalytic Reductive Coupling Strategies

Synthesis ◽  
2020 ◽  
Vol 52 (18) ◽  
pp. 2623-2638
Author(s):  
Joshua D. Sieber ◽  
Toolika Agrawal
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Short Review ◽  
Reductive Coupling ◽  
Recent Developments ◽  
Molecular Complexity ◽  
Metal Catalyzed ◽  
Coupling Processes ◽  
Coupling Strategies

Metal-catalyzed reductive coupling processes have emerged as a powerful methodology for the introduction of molecular complexity from simple starting materials. These methods allow for an orthogonal approach to that of redox-neutral strategies for the formation of C–C bonds by enabling cross-coupling of starting materials not applicable to redox-neutral chemistry. This short review summarizes the most recent developments in the area of metal-catalyzed reductive coupling utilizing catalyst turnover by a stoichiometric reductant that becomes incorporated in the final product.1 Introduction2 Ni Catalysis3 Cu Catalysis4 Ru, Rh, and Ir Catalysis4.1 Alkenes4.2 1,3-Dienes4.3 Allenes4.4 Alkynes4.5 Enynes5 Fe, Co, and Mn Catalysis6 Conclusion and Outlook

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

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