scholarly journals Weinreb Amides as Directing Groups for Transition Metal-Catalyzed C-H Functionalizations

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 830 ◽  
Author(s):  
Jagadeesh Kalepu ◽  
Lukasz Pilarski
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Metal Catalysts ◽  
Mechanistic Studies ◽  
Weinreb Amides ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Weinreb amides are a privileged, multi-functional group with well-established utility in classical synthesis. Recently, several studies have demonstrated the use of Weinreb amides as interesting substrates in transition metal-catalyzed C-H functionalization reactions. Herein, we review this part of the literature, including the metal catalysts, transformations explored so far and specific insights from mechanistic studies.

Phosphorus-Containing Groups Assisted Transition Metal Catalyzed C-H Activation Reactions

2019 ◽  
Vol 23 (2) ◽  
pp. 103-135 ◽  
Author(s):  
Chun-Ni Zhou ◽  
Zi-Ang Zheng ◽  
George Chang ◽  
Yuan-Chao Xiao ◽  
Yang-Huan Shen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Mechanistic Study ◽  
Recent Advances ◽  
Phosphorus Containing ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Over the last few decades, transition metal-catalyzed direct C-H activation with the assistance of a coordinating directing group has emerged as an atom- and stepeconomical synthetic tools to transform C–H bonds into carbon-carbon or carbonheteroatom bonds. Although the strategies involving regioselective C–H cleavage assisted by various directing groups have been extensively reviewed in the literature, we now attempt to give an overview of the recent advances on phosphorus-containing functional group assisted C-H activation reactions catalyzed by transition-metal catalysts including mechanistic study and synthetic applications. The discussion is directed towards C-H olefination, C-H activation/cyclization, C-H arylation, C-H amination, C-H hydroxylation and acetoxylation as well as miscellaneous C-H activation.

scholarly journals Transition metal-catalyzed organic reactions in undivided electrochemical cells

2021 ◽  
Author(s):  
Cong Ma ◽  
Ping Fang ◽  
Dong Liu ◽  
Ke-Jin Jiao ◽  
Pei-Sen Gao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Research Area ◽  
Metal Catalysts ◽  
Organic Reactions ◽  
Electrochemical Cells ◽  
Organic Electrochemistry ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Abstract: Transition metal-catalyzed organic electrochemistry is a rapidly growing research area owing in part of the ability of metal catalysts to alter the selectivity of a given transformation. This conversion...

Recent advance in NHC-palladium catalysis for alkynes chemistry: versatile synthesis and applications

2021 ◽  
Author(s):  
Jianxiao Li ◽  
Dan He ◽  
Zidong Lin ◽  
Wanqing Wu ◽  
Huanfeng Jiang
Keyword(s):  
Transition Metal ◽  
Palladium Catalysis ◽  
Metal Catalysts ◽  
Chemical Transformations ◽  
The Past ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

During the past decades, alkynes chemistry has attracted considerable attention owing to their unique and idiographic nucleophilic and electrophilic properties in transition-metal-catalyzed chemical transformations. Among the various metal catalysts, palladium...

Directing-Group-Assisted Transition-Metal-Catalyzed Direct C–H Oxidative Annulation of Arenes with Alkynes for Facile Construction of Various Oxygen Heterocycles

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 993-1006 ◽  
Author(s):  
Guanghua Kuang ◽  
Guangyuan Liu ◽  
Xingxing Zhang ◽  
Naihao Lu ◽  
Yiyuan Peng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Noble Metals ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Research Papers ◽  
Recent Advances ◽  
Oxygen Heterocycles ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The most recent advances in the construction of oxygen heterocycles by the directing-group-assisted transition-metal-catalyzed direct oxidative annulation of arenes with diverse alkynes are summarized in this review. More than 140 recent research papers and many closely related reviews are referenced in this paper. Nine different oxygen heterocycles frameworks are discussed. Several traditional transition-metal catalysts as well as some classical non-noble metals are utilized to promote the annulation. Three plausible controlling models are disclosed to clarify the excellent regioselectivity outcomes achieved in case of unsymmetrical alkyne substrates.1 Introduction2 Coumarins3 I socoumarins and Their Analogues4 2-Pyrones and Their Analogues5 Chromones and Chroman-4-ones6 Chromenes and Isochromenes7 Fused Polycyclic Oxygen Heteroaromatics8 Benzofurans, Dihydrobenzofurans, and Furans9 Phthalides and Benzofuranones10 Benzoxepines11 Conclusion

scholarly journals Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene

2019 ◽  
Vol 16 (4) ◽  
pp. 460-484 ◽  
Author(s):  
Rebecca Boutin ◽  
Samuel Koh ◽  
William Tam
Keyword(s):  
Transition Metal ◽  
Structural Features ◽  
Metal Catalysts ◽  
Single Step ◽  
Transition Metal Catalysts ◽  
Biologically Active ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Work Done

Background: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active. Objective: This review will provide an overview of transition metal-catalyzed reactions from the past couple of years including cobalt, copper, iridium, nickel, palladium and rhodium- catalyzed reactions. In addition, the recent derivatization of OBD to cyclopropanated oxabenzonorbornadiene and its reactivity will be discussed. Conclusion: It can be seen from the review, that the work done on this topic has employed the use of many different transition metal catalysts, with many different nucleophiles, to perform various transformations on the OBD molecule. Additionally, depending on the catalyst and ligand used, the stereo and regioselectivity of the product can be controlled, with proposed mechanisms to support the understanding of such reactions. The use of palladium has also generated a cyclopropanated OBD, with reactivity similar to that of OBD. An additional reactive site exists at the distal cyclopropane carbon, giving rise to three types of ring-opened products.

Cu(I)-Bis(phosphine) Dioxides as catalysts for the Enantioselective α-Arylation of Carbonyl Compounds

Synlett ◽  
2021 ◽  
Author(s):  
Margarita Escudero-Casao ◽  
Giulia Licini ◽  
Manuel Orlandi
Keyword(s):  
Reaction Mechanism ◽  
Transition Metal ◽  
Catalytic System ◽  
Carbonyl Compounds ◽  
Research Area ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The transition metal catalyzed α-arylation of carbonyl compounds was first reported by Buchwald and Hartwig in 1997. This transformation has been used and studied extensively over the last two decades. Enantioselective variants were also developed that allow for controlling the product stereochemistry. However, these suffer several limitations in the context of formation of tertiary stereocenters. Presented here is our group’s contribution to this research area. The chiral Cu-bis(phosphine) dioxides catalytic system that we reported allowed accessing the enantioselective α-arylation of ketones that were not suitable for this transformation before in good yields and er up to 97.5:2.5. Preliminary insight and speculation concerning the reaction mechanism involving the unusual pairing of bis(phosphine) dioxides with transition metal catalysts is also given.

Directed ortho Metalation (DoM)-Linked Corriu–Kumada, Negishi, and Suzuki–Miyaura Cross-Coupling Protocols: A Comparative Study

Synthesis ◽  
2018 ◽  
Vol 50 (22) ◽  
pp. 4395-4412 ◽  
Author(s):  
Victor Snieckus ◽  
Claude Quesnelle
Keyword(s):  
Transition Metal ◽  
Comparative Study ◽  
Systematic Study ◽  
Functional Group ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Ortho Metalation ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (DoM) is reported. In general, the Suzuki–Miyaura and Negishi protocols show greater scope and better yields than the Corriu–Kumada variant, although the latter qualitatively proceeds at fastest rate but has low functional group tolerance. The Negishi process is shown to be useful for substrates with nucleophile and base-sensitive functionality and it is comparable to the Suzuki–Miyaura reaction in efficiency. The link of these cross-coupling reactions to the DoM strategy lends itself to the regioselective construction of diversely substituted aromatics and heteroaromatics.

Recent Advances in the Synthesis of Acyl Fluorides

Synthesis ◽  
2020 ◽  
Author(s):  
Marie Gonay ◽  
Chloé Batisse ◽  
Jean-François Paquin
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Peptide Synthesis ◽  
Uranium Hexafluoride ◽  
Metal Catalysts ◽  
Recent Advances ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Nucleophilic Fluorination ◽  
Bromine Trifluoride

AbstractAcyl fluorides are valuable intermediates in organic synthesis. They are increasingly employed in peptide synthesis, in challenging esterification and amidation reactions or in transition-metal-catalyzed transformations. This review summarizes recent advances in their preparation.1 Introduction2 Nucleophilic Fluorination2.1 α-Fluoroamine Reagents2.2 Sulfur-Based Reagents2.3 Metal Catalysts2.4 Phosphorus-Based Reagents2.5 N,N′-Dicyclohexylcarbodiimide/HF·Pyridine2.6 Uranium Hexafluoride2.7 Bromine Trifluoride3 Radical Fluorination4 Conclusion

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