Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates with Arylboronic Acids

4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.Key words: palladium, cross-coupling, regioselectivity, quinolines, boronic acids.

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Sulfur-Ligand/Pd-Catalyzed Cross-Coupling Reactions of Aryl Halides with Arylboronic Acids Under Aerobic Conditions

Catalysis Letters ◽

10.1007/s10562-010-0342-z ◽

2010 ◽

Vol 137 (1-2) ◽

pp. 69-73 ◽

Cited By ~ 14

Author(s):

Hong-ling Li ◽

Zhi-sheng Wu ◽

Min Yang ◽

Yan-xing Qi

Keyword(s):

Cross Coupling ◽

Aryl Halides ◽

Coupling Reactions ◽

Aerobic Conditions ◽

Arylboronic Acids ◽

Cross Coupling Reactions ◽

Sulfur Ligand

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1,3-Phenylene-bis-(1H)-tetrazole Pincer Ligand for Palladium-Catalyzed Suzuki Cross-Coupling Reactions of Arylhalides with Arylboronic Acids

Synlett ◽

10.1055/s-2004-831303 ◽

2004 ◽

pp. 2227-2229 ◽

Cited By ~ 1

Author(s):

Chang Ho Oh ◽

Arun Kumar Gupta ◽

Chul Yun Rim

Keyword(s):

Cross Coupling ◽

Coupling Reactions ◽

Pincer Ligand ◽

Arylboronic Acids ◽

Cross Coupling Reactions ◽

Palladium Catalyzed

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Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates with Arylboronic Acids

Triphenylphosphine as a Ligand for Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Chlorides with Arylboronic Acids

ChemInform Abstract: Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature SuzukiâMiyaura and BuchwaldâHartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids.

Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids

ChemInform Abstract: Room Temperature Nickel(II) Complexes [(4-MeOC6H4)Ni-(PCy3)2OTs and Ni(PCy3)2X2]-Catalyzed Cross-Coupling Reactions of Aryl/Alkenyl Sulfonates with Arylboronic Acids.

Room Temperature Nickel(II) Complexes [(4-MeOC6H4)Ni(PCy3)2OTs and Ni(PCy3)2X2]-Catalyzed Cross-Coupling Reactions of Aryl/Alkenyl Sulfonates with Arylboronic Acids

Triphenylphosphine as a Ligand for Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Chlorides with Arylboronic Acids.

Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates with Arylboronic Acids.

Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

Sulfur-Ligand/Pd-Catalyzed Cross-Coupling Reactions of Aryl Halides with Arylboronic Acids Under Aerobic Conditions

1,3-Phenylene-bis-(1H)-tetrazole Pincer Ligand for Palladium-Catalyzed Suzuki Cross-Coupling Reactions of Arylhalides with Arylboronic Acids

ChemInform Abstract: Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature SuzukiâMiyaura and BuchwaldâHartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids.