Phosphine-free hydrazone-Pd complex as the catalyst precursor for a Suzuki-Miyaura reaction under mild aerobic
Takashi Mino1, Yoshiaki Shirae, Masami Sakamoto
1Department of Applied Chemistry and Biotechnology, Faculty of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. tmino@faculty.chiba-u.jp
Abstract:
[reaction: see text] Glyoxal bis(N-methyl-N-phenylhydrazone) (1) and its related compounds such as 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone (3) were prepared and examined as ligands for the Suzuki-Miyaura cross-coupling reaction of aryl halides and arylboronic acids. We found phosphine-free catalysts, such as Pd(OAc)(2)/hydrazone ligand 1 or 3, to be efficient catalysts for a variety of substrates to produce the coupling products in good yields.
More Related Videos
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Preparation and Reactions of Thiols
Preparation and Reactions of Sulfides
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)

![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)