Steric and Electronic Effects Influencing β-Aryl Elimination in the Pd-catalyzed Carbon–Carbon Single Bond Activation of Triarylmethanols

2013 ◽  
Vol 78 (4) ◽  
pp. 1665-1669 ◽  
Author(s):  
James R. Bour ◽  
Jacob C. Green ◽  
Valerie J. Winton ◽  
Jeffrey B. Johnson
Keyword(s):  
Bond Activation ◽  
Single Bond ◽  
Electronic Effects

Pyridine-directed carbon-carbon single bond activation: rhodium-catalyzed decarbonylation of aryl and heteroaromatic ketones

2021 ◽  
pp. 153132
Author(s):  
Cole J. Wagner ◽  
Eric A. Salisbury ◽  
Erik J. Schoonover ◽  
Jacob P. VanderRoest ◽  
Jeffrey B. Johnson
Keyword(s):  
Bond Activation ◽  
Single Bond

The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation

2020 ◽  
Vol 26 (1) ◽  
pp. 20-25
Author(s):  
Xinyi Zhao ◽  
Hongge Jia ◽  
Qingji Wang ◽  
Heming Song ◽  
Yanan Tang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Oxidative Coupling ◽  
Bond Activation ◽  
Coupling Reaction ◽  
Reaction Yield ◽  
Rhodium Complexes ◽  
Electronic Effects ◽  
Oxidative Coupling Reaction ◽  
Excellent Activity ◽  
Benzaldehyde Derivatives

AbstractThis paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylalanine, l-valine or l-proline; cod is 1,5-cyclooctadiene) to obtain chromones in 12.7–88.3% yield. These new Rh catalysts have excellent activity for the coupling reaction between phenylacetylene and different benzaldehyde derivatives. It was found that the electronic effects of the benzaldehyde derivative substituent affected the reaction yield, which is in accordance with the proposed mechanism.

Iron-catalysed carbon–carbon single bond activation

2013 ◽  
Vol 11 (8) ◽  
pp. 1271 ◽  
Author(s):  
Johannes E. M. N. Klein ◽  
Bernd Plietker
Keyword(s):  
Bond Activation ◽  
Single Bond

Challenging metal-based transformations. From single-bond activation to catalysis and metallaquinonoids

2003 ◽  
Vol 75 (4) ◽  
pp. 445-460 ◽  
Author(s):  
D. Milstein
Keyword(s):  
Bond Activation ◽  
Single Step ◽  
Catalytic Reactions ◽  
Single Bond ◽  
Quinone Methides ◽  
Pd Catalysts ◽  
Biologically Relevant ◽  
Aryl Chlorides ◽  
Metal Insertion ◽  
Aluminum Alkyls

Catalytic reactions resulting from our C–X (X = H, C, O, N, halide) bond activation studies are described. Aryl chlorides can react with aluminum alkyls in preference to bromides. Using PCP-type Pd catalysts, Heck reaction with aryl iodides and bromides can proceed without involvement of Pd(0). Ru-catalyzed oxidative coupling of arenes with alkenes using O2 was accomplished. Using specifically designed systems, the scope and mechanisms of C–C activation in solution was studied and compared to C–H activation. C–C activation by Rh(I), Ir(I), Ni(II),Pt(II), Ru(II), and Os(II) was observed. Metal insertion into a strong C–C bond can be kinetically and thermodynamically more favorable than the competing C–H activation. Selective, single-step oxidative addition of a strong C–C bond to a metal was observed and kinetically evaluated. Catalytic C–C hydrogenolysis was demonstrated. A combination of C–C activation and C–R formation (R = aryl, silyl) resulted in unusual methylene transfer chemistry. Selective activation of aryl–O and Me–O bonds was observed. New types of interactions between metals and arenes and unusual quinonoid complexes, including quinone methides, xylylenes, methylene arenium, and a metallaquinone, were discovered. C–H and C–C agostic complexes of cationic metals, proposed as intermediates in bond activation, were isolated. Stabilization and controlled release of biologically relevant, extremely unstable, simple quinone methides, was accomplished.

ChemInform Abstract: Iron-Catalyzed Carbon-Carbon Single Bond Activation

ChemInform ◽  
2013 ◽  
Vol 44 (27) ◽  
pp. no-no
Author(s):  
Johannes E. M. N. Klein ◽  
Bernd Plietker
Keyword(s):  
Bond Activation ◽  
Single Bond

Twofold CC Single Bond Activation and Cleavage in the Reaction of Octatetraynes with Titanocene and Zirconocene Complexes

1997 ◽  
Vol 36 (23) ◽  
pp. 2615-2617 ◽  
Author(s):  
Paul-Michael Pellny ◽  
Normen Peulecke ◽  
Vladimir V. Burlakov ◽  
Annegret Tillack ◽  
Wolfgang Baumann ◽  
...  
Keyword(s):  
Bond Activation ◽  
Single Bond
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