Transition-metal catalyzed oxidative cross-coupling reactions to form C–C bonds involving organometallic reagents as nucleophiles

2011 ◽  
Vol 40 (5) ◽  
pp. 2761 ◽  
Author(s):  
Wei Shi ◽  
Chao Liu ◽  
Aiwen Lei
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Organometallic Reagents ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3714-3734
Author(s):  
Zhi-Bing Dong ◽  
Jin-Quan Chen
Keyword(s):  
Transition Metal ◽  
Nucleophilic Addition ◽  
Cross Coupling ◽  
Addition Reactions ◽  
Nucleophilic Additions ◽  
Coupling Reactions ◽  
Organometallic Reagents ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractOrganometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.Introduction1 Transition-Metal-Catalyzed Cross Couplings Involving Organo­zinc Reagents2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents3 Transition-Metal-Free Cross Couplings Involving Zn and Mg ­Organometallic Reagents4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics6 Conclusion

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
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