Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines

Rao, K. Penta; Basak, A. K.; Raju, Amancha; Patil, Vikas; Reddy, L. Krishnakanth

doi:10.1016/j.tetlet.2013.07.149

Cited by 15 publications

(4 citation statements)

References 34 publications

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“…Compared with the Co 2 (CO) 8 -catalyzed or -mediated carbonylation of EDA with CO involving the formation of ketene intermediate, − the Pd-catalyzed protocol provides a general route to ketene compounds and is expected to be widely used in organic synthesis owing to the broad substrate scope of carbene precursors and the mild reaction conditions (with atmospheric pressure of CO). Later, similar transformations were also achieved under the catalysis of other transition-metal complexes. − …”

Section: Pd-catalyzed Carbene Coupling Reactionsmentioning

confidence: 99%

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

2017

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Transition-metal-catalyzed cross-coupling reactions have been well-established as indispensable tools in modern organic synthesis. One of the major research goals in cross-coupling area is expanding the scope of the coupling partners. In the past decade, diazo compounds (or their precursors N-tosylhydrazones) have emerged as nucleophilic cross-coupling partners in C-C single bond or C═C double bond formations in transition-metal-catalyzed reactions. This type of coupling reaction involves the following general steps. First, the organometallic species is generated by various processes, including oxidative addition, transmetalation, cyclization, C-C bond cleavage, and C-H bond activation. Subsequently, the organometallic species reacts with the diazo substrate to generate metal carbene intermediate, which undergoes rapid migratory insertion to form a C-C bond. The new organometallic species generated from migratory insertion may undergo various transformations. This type of carbene-based coupling has proven to be general: various transition metals including Pd, Cu, Rh, Ni, Co, and Ir are effective catalysts; the scope of the reaction has also been extended to substrates other than diazo compounds; and various cascade processes have also been devised based on the carbene migratory insertion. This review will summarize the achievements made in this field since 2001.

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Section: Pd-catalyzed Carbene Coupling Reactionsmentioning

confidence: 99%

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

2017

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“…Characterization of these compounds was achieved by using standard spectroscopic and analytical techniques as well as crystal structure analysis for four of the products. [34][35][36] Considering the importance of amido esters and amido phosphonates, and in continuation of our research on carbenes, [37][38][39][40] we herein report an efficient method for the synthesis of amido esters and amido phosphonates that proceeds through the carbonylation of carbenes by using a nongaseous CO source followed by a nucleophilic addition reaction using different amines. [21,26] The synthesis of ketenes by the carbonylation of carbenes using carbon monoxide offers several advantages when other known methods suffer from low yields and harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 96%

Synthesis of Amido Esters and Amido Phosphonates through Carbonylation of Diazo Compounds Followed by Nucleophilic Addition Reaction

Ramakrishna

Sivasankar

2017

Eur J Org Chem

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We report a method to produce amido esters and amido phosphonates. Octacarbonyldicobalt [Co2(CO)8] was found to be an efficient nongaseous CO source that could be used as a reagent for the carbonylation of diazo esters and diazo phosphonates under mild reaction conditions. A number of diazo esters and diazo phosphonates smoothly underwent the reaction with CO, which was generated from Co2(CO)8, to produce the corresponding ketenes. The subsequent reaction with an amine afforded the expected amido esters and phosphonates. By applying the developed protocol, we synthesized a number of amido esters and amido phosphonates. Characterization of these compounds was achieved by using standard spectroscopic and analytical techniques as well as crystal structure analysis for four of the products.

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“…Thus, the microwave-assisted carbonylation/amination cascade reaction of N-tosylhydrazones gave N-benzylamides [Scheme 49 (b)]. 99 Furthermore, Pathak and coworkers expanded on this method to synthesize substituted indolin-2-one and azaindolin-2-one derivatives via intramolecular carbonylation/amination of 2-aminobenzaldehyde-derived N-tosylhydrazones. 100…”

Section: Scheme 48 Rh(ii)-catalyzed Reaction Of N-tosylhydrazones Andmentioning

confidence: 99%

An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions

2018

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N-Tosylhydrazones have had widespread application in organic synthesis for more than a half century. In most of cases, N-tosylhydrazones, as masked diazo compounds, have been generally used in a series of important carbon–carbon and carbon–heteroatom bond-forming reactions. This review provides an update on progress in diverse coupling reactions of N-tosylhydrazones since 2012. The examples selected are mainly categorized by metal-catalyzed and metal-free systems, wherein four main types of transformations including insertion, olefination, alkynylation, and cyclization are discussed for each system.1 Introduction2 Transition-Metal-Catalyzed Coupling Reactions3 Metal-Free Coupling Reactions4 Conclusion and Outlook

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Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines

Cited by 15 publications

References 34 publications

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

Synthesis of Amido Esters and Amido Phosphonates through Carbonylation of Diazo Compounds Followed by Nucleophilic Addition Reaction

An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions

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