Ruthenium-catalyzed C(sp2)-H ortho-heteroarylation of 2-arylphthalazin-1(2H)-one using five-membered heteroarenes by
Alagumalai Ramkumar1, Thirumanavelan Gandhi1
1Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore, Tamil Nadu-632014, India. velan.g@vit.ac.in.
Abstract:
The cross-dehydrogenative coupling reactions have gained supreme importance owing to their synthetic efficiency in accessing simple to complex organic molecules. Herein, we report a Ru(II)-catalyzed directing group-assisted CDC reaction between 2-arylphthalazin-1(2H)-one and heteroarenes. This methodology offers advantages such as excellent regio-selectivity with good functional group compatibility, resulting in a broad substrate scope. Mechanistically, Ru(II)-catalyzed ortho-C(sp2)-H cross-coupling operates via a concerted metalation-deprotonation (CMD) mechanism.
Related Concept Videos
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)

