γ-Selective Cross-Coupling Reactions of Potassium Allyltrifluoroborates with Haloarenes Catalyzed by a Pd(0)/D-t-BPF or Pd(0)/Josiphos ((R,S)-CyPF-t-Bu) Complex: Mechanistic Studies on Transmetalation and Enantioselection

2009 ◽  
Vol 28 (1) ◽  
pp. 152-160 ◽  
Author(s):  
Yasunori Yamamoto ◽  
Shingo Takada ◽  
Norio Miyaura ◽  
Tetsuji Iyama ◽  
Hiroto Tachikawa
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Mechanistic Studies ◽  
Cross Coupling Reactions

scholarly journals Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1,3-butadiene: mechanistic studies of four-component coupling and competing cross-coupling reactions

2018 ◽  
Vol 9 (8) ◽  
pp. 2195-2211 ◽  
Author(s):  
Takanori Iwasaki ◽  
Asuka Fukuoka ◽  
Wataru Yokoyama ◽  
Xin Min ◽  
Ichiro Hisaki ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Mechanistic Studies ◽  
Theoretical Methods ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Detailed Reaction Mechanism

The detailed reaction mechanism of anionic Ni complex-promoted C–C bond forming reactions was clarified by experimental and theoretical methods.

scholarly journals Reactant-Induced Photoactivation of a Gold-Catalyzed Csp2-Csp Cross-Coupling Leading to Indoles

2021 ◽  
Author(s):  
Fen Zhao ◽  
Mehdi Abdellaoui ◽  
Jérome Berthet ◽  
Vincent Corcé ◽  
Stéphanie Delbaere ◽  
...  
Keyword(s):  
Reaction Medium ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Wide Scope ◽  
Mechanistic Studies ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Post Functionalization

A novel access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process was observed. Of note, 2-iodo-ynamides that have never been used in any organometallic cross-coupling reaction could be used as electrophiles. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converged on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.

scholarly journals Reactant-Induced Photoactivation of a Gold-Catalyzed Csp2-Csp Cross-Coupling Leading to Indoles

2021 ◽  
Author(s):  
Fen Zhao ◽  
Mehdi Abdellaoui ◽  
Jérome Berthet ◽  
Vincent Corcé ◽  
Stéphanie Delbaere ◽  
...  
Keyword(s):  
Reaction Medium ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Wide Scope ◽  
Mechanistic Studies ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Post Functionalization

A novel access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process was observed. Of note, 2-iodo-ynamides that have never been used in any organometallic cross-coupling reaction could be used as electrophiles. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converged on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.

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