Related Experiment Video
Updated: Jan 15, 2026
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Photochemical Ni-Catalyzed Selective Mono-N-Arylation
Geyang Song1, Ding-Zhan Nong1, Gang Li1
1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
Abstract:
The selective synthesis of N-monomethyl arylamines presents an important challenge in synthetic chemistry. Furthermore, small molecule amines readily coordinate with metal catalysts, causing catalyst deactivation. In this work, we report an efficient C-N coupling reaction of (hetero)aryl halides with small molecule amine salts. Without the need for an external photosensitizer in the presence of a soluble organic base, a bipyridine-Ni(II) complex serving as a catalyst successfully enables the selective C-N coupling of (hetero)aryl halides with methylamine, deuterated methylamine, ethylamine, and dimethylamine under purple light irradiation (390-395 nm), thus preventing catalyst deactivation. Mechanistic studies reveal that the reaction proceeds via a Ni(I)-Ni(III) catalytic cycle, and more than 100 examples showcase its feasibility and versatility in organic synthesis.
![[DPEPhosbcpCu]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)
Related Concept Videos
01:30Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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.
01:21Acid-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...