Suzuki–Miyaura Cross-Coupling of Heteroaryl Halides and Arylboronic Acids in Continuous Flow

2011 ◽  
Vol 13 (19) ◽  
pp. 5180-5183 ◽  
Author(s):  
Timothy Noël ◽  
Andrew J. Musacchio
Keyword(s):  
Continuous Flow ◽  
Cross Coupling ◽  
Arylboronic Acids

scholarly journals Cu(OTf)2‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products

2021 ◽  
Author(s):  
Allan J. B. Watson ◽  
Nicola L. Bell ◽  
Chao Xu ◽  
James W. B. Fyfe ◽  
Julien C. Vantourout ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Arylboronic Acids

Novel and Unexpected Deamination during the Palladium-Catalysed Cross-Coupling of Haloanilines and Arylboronic Acids

Synlett ◽  
1999 ◽  
Vol 1999 (4) ◽  
pp. 438-440 ◽  
Author(s):  
Michael Hird ◽  
Alexander J. Seed ◽  
Kenneth J. Toyne
Keyword(s):  
Cross Coupling ◽  
Arylboronic Acids

Continuous Flow Palladium(II)-Catalyzed Oxidative Heck Reactions with Arylboronic Acids

2010 ◽  
Vol 2010 (12) ◽  
pp. 2270-2274 ◽  
Author(s):  
Luke R. Odell ◽  
Jonas Lindh ◽  
Tomas Gustafsson ◽  
Mats Larhed
Keyword(s):  
Continuous Flow ◽  
Heck Reactions ◽  
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

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble
Keyword(s):  
Phenylboronic Acid ◽  
Palladium Catalysis ◽  
Suzuki Reaction ◽  
Tetrabutylammonium Bromide ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

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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