ChemInform Abstract: Palladium Catalyzed Asymmetric Suzuki-Miyaura Coupling Reactions to Axially Chiral Biaryl Compounds: Chiral Ligands and Recent Advances

ChemInform ◽  
2015 ◽  
Vol 46 (48) ◽  
pp. no-no
Author(s):  
Dao Zhang ◽  
Quanrui Wang
Keyword(s):  
Chiral Ligands ◽  
Coupling Reactions ◽  
Recent Advances ◽  
Axially Chiral ◽  
Palladium Catalyzed ◽  
Biaryl Compounds

Synthesis and application of P,olefin type axially chiral ligands with sec-alkyl groups

2019 ◽  
Vol 17 (6) ◽  
pp. 1455-1465 ◽  
Author(s):  
Takashi Mino ◽  
Daiki Yamaguchi ◽  
Chihiro Masuda ◽  
Junpei Youda ◽  
Toshibumi Ebisawa ◽  
...  
Keyword(s):  
Chiral Ligands ◽  
Chiral Ligand ◽  
Allylic Substitution ◽  
Alkyl Groups ◽  
Axially Chiral ◽  
Palladium Catalyzed

Palladium-catalyzed asymmetric allylic substitution with indoles using a chiral ligand 3b, which have fewer hindered substituents such as secondary alkyl groups than 1-adamantyl group, gave desired products (R)-9 with high enantioselectivities (up to 96% ee).

scholarly journals Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position

2020 ◽  
Vol 16 ◽  
pp. 966-973
Author(s):  
Yongsu Li ◽  
Bendu Pan ◽  
Xuefeng He ◽  
Wang Xia ◽  
Yaqi Zhang ◽  
...  
Keyword(s):  
Steric Hindrance ◽  
Coupling Reactions ◽  
Mild Conditions ◽  
Axially Chiral ◽  
High Yields ◽  
Very High ◽  
Significant Superiority ◽  
Biaryl Compounds

Pd-catalyzed asymmetric Suzuki–Miyaura couplings of 3-methyl-2-bromophenylamides, 3-methyl-2-bromo-1-nitrobenzene and 1-naphthaleneboronic acids have been successfully developed and the corresponding axially chiral biaryl compounds were obtained in very high yields (up to 99%) with good enantioselectivities (up to 88% ee) under mild conditions. The chiral-bridged biphenyl monophosphine ligands developed by our group exhibit significant superiority to the naphthyl counterpart MOP in both reactivity and enantioselectivity control. The large steric hindrance from π-conjugated ortho-substituents of the bromobenzene substrates and the Pd···O interaction between carbonyl and palladium seem essential to achieve high enantioselectivity.

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