Decarboxylative Coupling Reactions

2010 ◽  
Vol 50 (5-6) ◽  
pp. 617-629 ◽  
Author(s):  
Lukas J. Goossen ◽  
Florence Collet ◽  
Käthe Goossen
Keyword(s):  
Coupling Reactions ◽  
Decarboxylative Coupling

Ruthenium(ii)-catalyzed decarbonylative and decarboxylative coupling of isatoic anhydrides with salicylaldehydes: access to aryl 2-aminobenzoates

2021 ◽  
Vol 19 (12) ◽  
pp. 2725-2730
Author(s):  
Bidisha R. Bora ◽  
Rashmi Prakash ◽  
Sabera Sultana ◽  
Sanjib Gogoi
Keyword(s):  
Coupling Reactions ◽  
Decarboxylative Coupling

Decarbonylative and decarboxylative coupling reactions of salicylaldehydes with isatoic anhydrides afford aryl 2-aminobenzoates.

Aryl Chlorides as Coupling Partners in the Palladium-catalyzed Decarboxylative Coupling Reactions of Propiolic Acids

2017 ◽  
Vol 38 (11) ◽  
pp. 1368-1371 ◽  
Author(s):  
Ju-Hyeon Lee ◽  
Gabriel Charles Edwin Raja ◽  
Jimin Kim ◽  
Kye Chun Nam ◽  
Sunwoo Lee
Keyword(s):  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Decarboxylative Coupling ◽  
Palladium Catalyzed

scholarly journals Gas-phase studies of metal catalyzed decarboxylative cross-coupling reactions of esters

2015 ◽  
Vol 87 (4) ◽  
pp. 391-404 ◽  
Author(s):  
Richard A.J. O’Hair
Keyword(s):  
Dft Calculations ◽  
Metal Complex ◽  
Gas Phase ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Allyl Acetate ◽  
Metal Acetate ◽  
Cross Coupling Reactions ◽  
Decarboxylative Coupling ◽  
Metal Catalyzed

AbstractMetal-catalyzed decarboxylative coupling reactions of esters offer new opportunities for formation of C–C bonds with CO2as the only coproduct. Here I provide an overview of: key solution phase literature; thermochemical considerations for decarboxylation of esters and thermolysis of esters in the absence of a metal catalyst. Results from my laboratory on the use of multistage ion trap mass spectrometry experiments and DFT calculations to probe the gas-phase metal catalyzed decarboxylative cross-coupling reactions of allyl acetate and related esters are then reviewed. These studies have explored the role of the metal carboxylate complex in the gas phase decarboxylative coupling of allyl acetate proceeding via a simple two-step catalytic cycle. In Step 1, an organometallic ion, [CH3ML]+/–(where M is a group 10 or 11 metal and L is an auxillary ligand), is allowed to undergo ion-molecule reactions with allyl acetate to generate 1-butene and the metal acetate ion, [CH3CO2ML]+/–. In Step 2, the metal acetate ion is subjected to collision-induced dissociation to reform the organometallic ion and thereby close the catalytic cycle. DFT calculations have been used to explore the mechanisms of these reactions. The organometallic ions [CH3CuCH3]–, [CH3Cu2]+, [CH3AgCu]+and [CH3M(phen)]+(where M = Ni, Pd and Pt) all undergo C–C bond coupling reactions with allyl acetate (Step 1), although the reaction efficiencies and product branching ratios are highly dependant on the nature of the metal complex. For example, [CH3Ag2]+does not undergo C–C bond coupling. Using DFT calculations, a diverse range of mechanisms have been explored for these C–C bond-coupling reactions including: oxidative-addition, followed by reductive elimination; insertion reactions and SN2-like reactions. Which of these mechanisms operate is dependant on the nature of the metal complex. A wide range of organometallic ions can be formed via decarboxylation (Step 2) although these reactions can be in competition with other fragmentation channels. DFT calculations have located different types of transition states for the formation of [CH3CuCH3]–, [CH3Cu2]+, [CH3AgCu]+and [CH3M(phen)]+(where M = Ni, Pd and Pt). Of the catalysts studied to date, [CH3Cu2]+and [CH3Pd(phen)]+are best at promoting C–C bond formation (Step 1) as well as being regenerated (Step 2). Preliminary results on the reactions of [C6H5M(phen)]+(M = Ni and Pd) with C6H5CO2CH2CH=CH2and C6H5CO2CH2C6H5are described.

ChemInform Abstract: Copper-Catalyzed Decarboxylative Coupling Reactions for the Synthesis of Propargyl Amines.

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Jeongah Lim ◽  
Kyungho Park ◽  
Aleum Byeun ◽  
Sunwoo Lee
Keyword(s):  
Coupling Reactions ◽  
Decarboxylative Coupling

Copper-Catalyzed Double Decarboxylative Coupling Reactions of Alkynyl Carboxylic Acid and Glyoxylic Acid: Synthesis of Propargyl Amines and Imidazopyridines

2016 ◽  
Vol 5 (6) ◽  
pp. 770-777 ◽  
Author(s):  
Jinseop Choi ◽  
Jeongah Lim ◽  
Francis Mariaraj Irudayanathan ◽  
Han-Sung Kim ◽  
Jaerim Park ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Glyoxylic Acid ◽  
Acid Synthesis ◽  
Coupling Reactions ◽  
Decarboxylative Coupling
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