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

scholarly journals Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (20) ◽  
pp. 4586-4598 ◽  
Author(s):  
Martyn Henry ◽  
Mohamed Mostafa ◽  
Andrew Sutherland
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.1 Introduction2 Intramolecular C–N Cross-Dehydrogenative Coupling2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation3 Intermolecular C–N Cross-Dehydrogenative Coupling3.1 ortho-C–N Bond Formation3.1.1 Copper-Catalyzed Reactions3.1.2 Other Transition-Metal-Catalyzed Reactions3.2 meta- and para-C–N Bond Formation4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds5 Conclusions

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

Transition-metal-catalyzed reactions of carbon-heteroatom bond formation by substitution and addition processes

2005 ◽  
Vol 77 (12) ◽  
pp. 2021-2027 ◽  
Author(s):  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Triple Bond ◽  
Bond Formation ◽  
Cross Coupling ◽  
Addition Reactions ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Two types of transition-metal-catalyzed cross-coupling reactions, which both lead to the formation of carbon-heteroatom bonds, are considered: RX + E-H and E-X + RM. The potential of addition reactions of E-H or E-E to double or triple bond in C-E bond formation is also demonstrated.

scholarly journals Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

2014 ◽  
Vol 10 ◽  
pp. 3031-3037 ◽  
Author(s):  
Kuppusamy Bharathimohan ◽  
Thanasekaran Ponpandian ◽  
A Jafar Ahamed ◽  
Nattamai Bhuvanesh
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Triazole Derivatives ◽  
One Pot Synthesis ◽  
Cross Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Herein, we describe a one-pot protocol for the synthesis of a novel series of polycyclic triazole derivatives. Transition metal-catalyzed decarboxylative CuAAC and dehydrogenative cross coupling reactions are combined in a single flask and achieved good yields of the respective triazoles (up to 97% yield). This methodology is more convenient to produce the complex polycyclic molecules in a simple way.

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

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