Base-catalyzed reactions. XXXIV. Alkali metal catalyzed side-chain aralkylation of 2- and 4-alkylpyridines with styrene, .alpha.-methylstyrene, and cis- and trans-.beta.-methylstyrene

1969 ◽  
Vol 34 (7) ◽  
pp. 2113-2118 ◽  
Author(s):  
Herman Pines ◽  
Nelson E. Sartoris
Keyword(s):  
Alkali Metal ◽  
Side Chain ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Cis And Trans

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.

Chemistry of Unsymmetrical C1-Substituted Oxabenzonorbornadienes

2021 ◽  
Vol 17 ◽  
Author(s):  
Austin Pounder ◽  
Angel Ho ◽  
Matthew Macleod ◽  
William Tam
Keyword(s):  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Substituent Effects ◽  
Face Selectivity ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Synthetic Intermediate

: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate which can be readily activated by transition metal complexes with great face selectivity due to its dual-faced nature and intrinsic angle strain on the alkene. To date, the understanding of transition-metal catalyzed reactions of OBD itself has burgeoned; however, this has not been the case for unsymmetrical OBDs. Throughout the development of these reactions, the nature of C1-substituent has proven to have a profound effect on both the reactivity and selectivity of the outcome of the reaction. Upon substitution, different modes of reactivity arise, contributing to the possibility of multiple stereo-, regio-, and in extreme cases, constitutional isomers which can provide unique means of constructing a variety of synthetically useful cyclic frameworks. To maximize selectivity, an understanding of bridgehead substituent effects is crucial. To that end, this review outlines hitherto reported examples of bridgehead substituent effects on the chemistry of unsymmetrical C1-substituted OBDs.

scholarly journals Transition metal-catalyzed reactions of N-sulfinyl imines

2021 ◽  
pp. 153104
Author(s):  
Francisco Foubelo ◽  
Carmen Nájera ◽  
José M. Sansano ◽  
Miguel Yus
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

scholarly journals Chiral Aziridine Sulfide N(sp3),S-Ligands for Metal-Catalyzed Asymmetric Reactions

Symmetry ◽  
2021 ◽  
Vol 13 (3) ◽  
pp. 502
Author(s):  
Agata J. Pacuła-Miszewska ◽  
Anna Laskowska ◽  
Anna Kmieciak ◽  
Mariola Zielińska-Błajet ◽  
Marek P. Krzemiński ◽  
...  
Keyword(s):  
Metal Binding ◽  
Electronic Effect ◽  
Asymmetric Reactions ◽  
Addition Reactions ◽  
Phenyl Sulfide ◽  
Enantiomeric Ratio ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Sulfide Group

A series of new bidentate N,S-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition reactions (up to 94.2:5.8) was obtained using the aziridine ligand bearing a p-nitro phenyl sulfide group. Collected results reveal a specific electronic effect that, by the presence of particular electron-donating or electron-withdrawing groups in the PhS- moiety, influences the σ-donor–metal binding and the enantioselectivity of the catalyzed reactions.

ChemInform Abstract: Metal-Catalyzed Reactions Between 2-Azabicyclo[2.2.1]hept-5-en-3-ones and Arylboronic Acids.

ChemInform ◽  
2010 ◽  
Vol 41 (42) ◽  
Author(s):  
Takumi Abe ◽  
Hiroyuki Takeda ◽  
Yumi Takahashi ◽  
Yoshihisa Miwa ◽  
Koji Yamada ◽  
...  
Keyword(s):  
Arylboronic Acids ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Iodide effects in transition metal catalyzed reactions

2004 ◽  
pp. 3409 ◽  
Author(s):  
Peter M. Maitlis ◽  
Anthony Haynes ◽  
Brian R. James ◽  
Marta Catellani ◽  
Gian Paolo Chiusoli
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed
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