Metal-Catalyzed Coupling Reactions on an Olefin Template:  The Total Synthesis of (13E,15E,18Z,20Z)-1-Hydroxypentacosa- 13,15,18,20-tetraen-11-yn-4-one 1-Acetate

2004 ◽  
Vol 69 (3) ◽  
pp. 695-700 ◽  
Author(s):  
Michael G. Organ ◽  
Haleh Ghasemi
Keyword(s):  
Total Synthesis ◽  
Coupling Reactions ◽  
Metal Catalyzed

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.

End-functionalization of dithiarubicene: Modulation of optoelectronic properties by metal-catalyzed coupling reactions and device application

2021 ◽  
Author(s):  
Kenji Tsukamoto ◽  
Koji Takagi ◽  
Keitaro Yamamoto ◽  
Yutaka Ie ◽  
Takanori Fukushima
Keyword(s):  
Optoelectronic Properties ◽  
Coupling Reactions ◽  
Device Application ◽  
Metal Catalyzed ◽  
Structure Properties

In order to modulate optoelectronic properties of dithiarubicene (DTR) by the end-functionalization and reveal the structure-properties relationship in detail, we have carried out a set of metal-catalyzed coupling reactions. Electron-withdrawing...

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

Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies

2006 ◽  
Vol 84 (10) ◽  
pp. 1226-1241 ◽  
Author(s):  
Peter Wipf ◽  
Michel Grenon
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Recent Progress ◽  
Furan Ring ◽  
Addition Reaction ◽  
Thermal Conditions ◽  
Preliminary Results ◽  
Keto Esters ◽  
New Methodologies ◽  
Metal Catalyzed

Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal-catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring formation either under thermal conditions or by microwave irradiation.Key words: 1,6-addition, organocuprates, catalytic desymmetrization, furan cyclization, microwave.

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