Related Experiment Video
Updated: Jul 17, 2025
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone
Hyotaik Kang1, Lida Tan2, Jing-Tan Han2
1Department of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street W., Montréal, Québec, H3A0B8, Canada. hyotaik.kang@mail.mcgill.ca.
Abstract:
Alkanes are naturally abundant chemical building blocks that contain plentiful C(sp3)-H bonds. While inert, the activation of C(sp3)-H via hydrogen atom abstraction (HAT) stages an appealing approach to generate alkyl radicals. However, prevailing shortcomings include the excessive use of oxidants and alkanes that impede scope. We herein show the use of gallium nitride (GaN) as a non-toxic, recyclable, heterogeneous photocatalyst to enable alkyl C(sp3)-H in conjunction with the catalytic use of simple photosensitizer, benzophenone, to promote the desired alkyl radical generation. The dual photocatalytic cycle enables cross-dehydrogenative Minisci alkylation under mild and chemical oxidant-free conditions.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
12:19Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Related Concept Videos
01:12Cycloaddition Reactions: MO Requirements for Photochemical Activation
02:17Reduction 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...
01:21Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
01:26Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
01:10Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism