scholarly journals On the Amine-Catalyzed Suzuki-Miyaura Coupling Using a Catalysis-Based Fluorometric Method

2021 ◽  
Author(s):  
Jincy K. Vinod ◽  
Annelise K. Wanner ◽  
Elizabeth James ◽  
Kazunori Koide
Keyword(s):  
Transition Metals ◽  
Recent Work ◽  
Organic Synthesis ◽  
Spectroscopic Analysis ◽  
Palladium Catalysis ◽  
Coupling Reactions ◽  
Fluorometric Method ◽  
Quantification Method ◽  
Phosphine Complex ◽  
Palladium Content

<p>The Suzuki-Miyaura coupling is one of the most frequently used reactions in organic synthesis. Recent work by others suggested that an arylamine, prepared by palladium catalysis and tricyclohexylphosphine, could catalyze Suzuki-Miyaura coupling reactions without transition metals. Herein, we used a fluorometric quantification method for palladium previously developed in our laboratory to unambiguously conclude that there is a correlation between the palladium content in the arylamine and the rate of a Suzuki-Miyaura coupling. Also, our mass spectroscopic analysis of the arylamine revealed the presence of a palladium-phosphine complex. When Pd(OAc)<sub>2</sub> was used as a catalyst for the same Suzuki-Miyaura coupling, tricyclohexylphosphine was detrimental to the coupling and that the arylamine played negligible role. This study demonstrates the utility of the fluorometric technology for catalysis research.<br></p>

scholarly journals On the Amine-Catalyzed Suzuki-Miyaura Coupling Using a Catalysis-Based Fluorometric Method

2021 ◽  
Author(s):  
Jincy K. Vinod ◽  
Annelise K. Wanner ◽  
Elizabeth James ◽  
Kazunori Koide
Keyword(s):  
Transition Metals ◽  
Recent Work ◽  
Organic Synthesis ◽  
Spectroscopic Analysis ◽  
Palladium Catalysis ◽  
Coupling Reactions ◽  
Fluorometric Method ◽  
Quantification Method ◽  
Phosphine Complex ◽  
Palladium Content

<p>The Suzuki-Miyaura coupling is one of the most frequently used reactions in organic synthesis. Recent work by others suggested that an arylamine, prepared by palladium catalysis, could catalyze Suzuki-Miyaura coupling reactions without transition metals. Herein, we used a fluorometric quantification method for palladium previously developed in our laboratory to unambiguously conclude that there is a correlation between the palladium content in the arylamine and the rate of a Suzuki-Miyaura coupling. Also, our mass spectroscopic analysis of the arylamine revealed the presence of a palladium-phosphine complex. We discovered that the phosphine was detrimental to the palladium catalysis and that the arylamine played negligible role. This study demonstrates the utility of the fluorometric technology for catalysis research.</p>

scholarly journals On the Amine-Catalyzed Suzuki-Miyaura Coupling Using a Catalysis-Based Fluorometric Method

2021 ◽  
Author(s):  
Jincy K. Vinod ◽  
Annelise K. Wanner ◽  
Elizabeth James ◽  
Kazunori Koide
Keyword(s):  
Transition Metals ◽  
Recent Work ◽  
Organic Synthesis ◽  
Spectroscopic Analysis ◽  
Palladium Catalysis ◽  
Coupling Reactions ◽  
Fluorometric Method ◽  
Quantification Method ◽  
Phosphine Complex ◽  
Palladium Content

<p>The Suzuki-Miyaura coupling is one of the most frequently used reactions in organic synthesis. Recent work by others suggested that an arylamine, prepared by palladium catalysis, could catalyze Suzuki-Miyaura coupling reactions without transition metals. Herein, we used a fluorometric quantification method for palladium previously developed in our laboratory to unambiguously conclude that there is a correlation between the palladium content in the arylamine and the rate of a Suzuki-Miyaura coupling. Also, our mass spectroscopic analysis of the arylamine revealed the presence of a palladium-phosphine complex. We discovered that the phosphine was detrimental to the palladium catalysis and that the arylamine played negligible role. This study demonstrates the utility of the fluorometric technology for catalysis research.</p>

Recent Applications of Continuous Flow in Homogeneous Palladium Catalysis

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3511-3529 ◽  
Author(s):  
Peter Koóš ◽  
Martin Markovič ◽  
Pavol Lopatka ◽  
Tibor Gracza
Keyword(s):  
Organic Synthesis ◽  
Continuous Flow ◽  
Palladium Catalysis ◽  
Flow Chemistry ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Flow Conditions ◽  
Cross Coupling Reactions ◽  
Continuous Flow Chemistry ◽  
Oxidative Transformations

Considerable advances have been made using continuous flow chemistry as an enabling tool in organic synthesis. Consequently, the number of articles reporting continuous flow methods has increased significantly in recent years. This review covers the progress achieved in homogeneous palladium catalysis using continuous flow conditions over the last five years, including C–C/C–N cross-coupling reactions, carbonylations and reductive/oxidative transformations.1 Introduction2 C–C Cross-Coupling Reactions3 C–N Coupling Reactions4 Carbonylation Reactions5 Miscellaneous Reactions6 Key to Schematic Symbols7 Conclusion

scholarly journals Iron-Catalyzed C–H Functionalizations under Triazole-Assistance

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1806 ◽  
Author(s):  
Matteo Lanzi ◽  
Gianpiero Cera
Keyword(s):  
Transition Metals ◽  
Organic Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Efficient Catalyst ◽  
Widespread Application ◽  
Promising Alternative ◽  
Cross Coupling Reactions ◽  
Benign Nature

3d transition metals-catalyzed C–H bond functionalizations represent nowadays an important tool in organic synthesis, appearing as the most promising alternative to cross-coupling reactions. Among 3d transition metals, iron found widespread application due to its availability and benign nature, and it was established as an efficient catalyst in organic synthesis. In this context, the use of ortho-orientating directing groups (DGs) turned out to be necessary for promoting selective iron-catalyzed C–H functionalization reactions. Very recently, triazoles DGs were demonstrated to be more than an excellent alternative to the commonly employed 8-aminoquinoline (AQ) DG, as a result of their modular synthesis as well as the mild reaction conditions applied for their removal. In addition, their tunable geometry and electronics allowed for new unprecedented reactivities in iron-catalyzed C–H activation methodologies that will be summarized within this review.

Organic synthesis with the most abundant transition metal–iron: from rust to multitasking catalysts

2021 ◽  
Author(s):  
Sujoy Rana ◽  
Jyoti Prasad Biswas ◽  
Sabarni Paul ◽  
Aniruddha Paik ◽  
Debabrata Maiti
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Organic Synthesis ◽  
Present Review ◽  
Synthetic Chemistry ◽  
Late Transition Metals ◽  
Iron Chemistry ◽  
Late Transition

The promising aspects of iron in synthetic chemistry are being explored for three-four decades as a green and eco-friendly alternative to late transition metals. This present review unveils these rich iron-chemistry towards different transformations.

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