Metal-catalyzed cross-coupling reactions with supported nanoparticles: Recent developments and future directions

2016 ◽  
Vol 58 (4) ◽  
pp. 439-496 ◽  
Author(s):  
Suellen D. T. de Barros ◽  
Jaqueline D. Senra ◽  
Elizabeth R. Lachter ◽  
Luiz Fernando B. Malta
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Future Directions ◽  
Supported Nanoparticles ◽  
Cross Coupling Reactions ◽  
Recent Developments ◽  
Metal Catalyzed

Sonochemistry in Transition Metal Catalyzed Cross-coupling Reactions: Recent Developments

2020 ◽  
Vol 23 (28) ◽  
pp. 3137-3153 ◽  
Author(s):  
Sankuviruthiyil M. Ujwaldev ◽  
K. R. Rohit ◽  
Sankaran Radhika ◽  
Gopinathan Anilkumar
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Reaction Rates ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Recent Developments ◽  
Ultrasound Assisted ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: Transition metal catalyzed cross-coupling reactions have always been very important in synthetic organic chemistry due to their versatility in forming all sorts of carbon-carbon and carbon-hetero atom bonds. Incorporation of ultrasound assistance to these protocols resulted in milder reaction conditions, faster reaction rates, etc. This review focuses on the contributions made by ultrasound-assisted protocols towards transition metal catalyzed crosscoupling reactions.

scholarly journals Photo-Induced Thiolate Catalytic Activation of Inert Caryl-Hetero Bonds for Radical Borylation

2020 ◽  
Author(s):  
Shun Wang ◽  
Hua Wang ◽  
Burkhard Koenig
Keyword(s):  
Bond Activation ◽  
Reducing Power ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Catalytic Activation ◽  
Cross Coupling Reactions ◽  
Recent Developments ◽  
Leaving Groups ◽  
Metal Catalyzed

Cross-coupling reactions are essential tools in modern synthesis of drugs, natural products and materials. The recent developments in photocatalytic radical generation have improved and expanded the classic metal-catalyzed cross coupling reactions even further. However, for sp<sup>2</sup> cross coupling reactions aryl halides or related active leaving groups, such as triflates, are required. Substituted arenes bearing strong C-X bonds remain inert to current methods. We describe now a new thiolate photocatalysis for the activation of inert substituted arenes in ipso-borylation reactions. This catalytic system exhibits strong reducing power and allows the borylation of stable C<sub>aryl</sub>−F, C<sub>aryl</sub>−O, C<sub>aryl</sub>-N and C<sub>aryl</sub>−S bonds, which are considered as chemically stable at mild reaction conditions. Our method considerably widens the available substrate scope of aryl radical precursors and we anticipate that this report will inspire new chemistry based on inert chemical bond activation.

scholarly journals Photo-Induced Thiolate Catalytic Activation of Inert Caryl-Hetero Bonds for Radical Borylation

2020 ◽  
Author(s):  
Shun Wang ◽  
Hua Wang ◽  
Burkhard Koenig
Keyword(s):  
Bond Activation ◽  
Reducing Power ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Catalytic Activation ◽  
Cross Coupling Reactions ◽  
Recent Developments ◽  
Leaving Groups ◽  
Metal Catalyzed

Cross-coupling reactions are essential tools in modern synthesis of drugs, natural products and materials. The recent developments in photocatalytic radical generation have improved and expanded the classic metal-catalyzed cross coupling reactions even further. However, for sp<sup>2</sup> cross coupling reactions aryl halides or related active leaving groups, such as triflates, are required. Substituted arenes bearing strong C-X bonds remain inert to current methods. We describe now a new thiolate photocatalysis for the activation of inert substituted arenes in ipso-borylation reactions. This catalytic system exhibits strong reducing power and allows the borylation of stable C<sub>aryl</sub>−F, C<sub>aryl</sub>−O, C<sub>aryl</sub>-N and C<sub>aryl</sub>−S bonds, which are considered as chemically stable at mild reaction conditions. Our method considerably widens the available substrate scope of aryl radical precursors and we anticipate that this report will inspire new chemistry based on inert chemical bond activation.

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.

Synthesis of Marine Polyacetylenes Callyberynes A−C by Transition-Metal-Catalyzed Cross-Coupling Reactions to sp Centers

2006 ◽  
Vol 71 (7) ◽  
pp. 2802-2810 ◽  
Author(s):  
Susana López ◽  
Francisco Fernández-Trillo ◽  
Pilar Midón ◽  
Luis Castedo ◽  
Carlos Saá
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

scholarly journals Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis

2015 ◽  
Vol 112 (39) ◽  
pp. 12026-12029 ◽  
Author(s):  
Yohei Yamashita ◽  
John C. Tellis ◽  
Gary A. Molander
Keyword(s):  
Small Molecules ◽  
Functional Group ◽  
Cross Coupling ◽  
Differential Protection ◽  
Coupling Reactions ◽  
Protecting Group ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Rapid Construction ◽  
Metal Catalyzed

Orthogonal reactivity modes offer substantial opportunities for rapid construction of complex small molecules. However, most strategies for imparting orthogonality to cross-coupling reactions rely on differential protection of reactive sites, greatly reducing both atom and step economies. Reported here is a strategy for orthogonal cross-coupling wherein a mechanistically distinct activation mode for transmetalation of sp3-hybridized organoboron reagents enables C-C bond formation in the presence of various protected and unprotected sp2-hybridized organoborons. This manifold has the potential for broad application, because orthogonality is inherent to the activation mode itself. The diversification potential of this platform is shown in the rapid elaboration of a trifunctional lynchpin through various transition metal-catalyzed processes without nonproductive deprotection or functional group manipulation steps.

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