74480-82-3

Upstream product

• 74480-64-1 N-Benzyl-N-(2-chloro-phenyl)-2-methyl-acrylamide 
• 124-38-9 carbon dioxide 
• 348-54-9 2-Fluoroaniline 
• 125509-82-2 N-(2-fluorophenyl)methacrylamide 
• 98018-66-7 N-benzyl-2-chloroaniline 

Relevant academic research and scientific papers

N-Heterocyclic Carbene-Catalyzed Truce-Smiles Rearrangement of N-Arylacrylamides via the Cleavage of Unactivated C(aryl)-N Bonds

We report on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, in which an unactivated C(aryl)-N bond is cleaved, leading to the formation of a new C(aryl)-C bond. The key to the success of this reaction is the

Nickel-Catalyzed Asymmetric Reductive Carbo-Carboxylation of Alkenes with CO2

Reductive carboxylation of organo (pseudo)halides with CO2 is a powerful method to provide carboxylic acids quickly. Notably, the catalytic reductive carbo-carboxylation of unsaturated hydrocarbons via CO2 fixation is a highly challenging but desirable approach for structurally diverse carboxylic acids. There are only a few reports and no examples of alkenes via transition metal catalysis. We report the first asymmetric reductive carbo-carboxylation of alkenes with CO2 via nickel catalysis. A variety of aryl (pseudo)halides, such as aryl bromides, aryl triflates and inert aryl chlorides of particular note, undergo the reaction smoothly to give important oxindole-3-acetic acid derivatives bearing a C3-quaternary stereocenter. This transformation features mild reaction conditions, wide substrate scope, facile scalability, good to excellent chemo-, regio- and enantioselectivities. The method highlights the formal synthesis of (?)-Esermethole, (?)-Physostigmine and (?)-Physovenine, and the total synthesis of (?)-Debromoflustramide B, (?)-Debromoflustramine B and (+)-Coixspirolactam A; thereby, opening an avenue for the total synthesis of chiral natural products with CO2.

N-Heterocyclic Carbene Catalyzed Concerted Nucleophilic Aromatic Substitution of Aryl Fluorides Bearing α,β-Unsaturated Amides

Concerted nucleophilic aromatic substitution (CSNAr) has emerged as a powerful mechanistic manifold, in which nucleophilic aromatic substitution can proceed in one step without the need to form a Meisenheimer intermediate. However, all of the CSNAr reactions reported thus far require a stoichiometric strong base or activating reagent, and no catalytic variants have yet been reported. Herein, we report an N-heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of acrylamides that contain a 2-fluorophenyl group on the nitrogen through a CSNAr reaction. By using this catalytic method, it is possible to synthesize an array of quinolin-2-one derivatives, which are common structural motifs in pharmaceuticals and organic materials. DFT calculations unambiguously revealed that this reaction proceeds through the concerted nucleophilic aromatic substitution of aryl fluorides, in which a stereoelectronic σ (Cipso-Cβ)→ σ*(Cipso-F) interaction critically contributes to the stabilization of the transition state for the cyclization.

Photocyclisation of Enamides. Part 14. Substituent Effects in the Photocyclisation of N-α,β-Unsaturated Acylanilides.

Irradiation of N-α,β-unsaturated acylanilides having various substituents on the benzene ring yielded a mixture of cis- and trans-octahydrophenanthridones (3a-f) and dihydroquinolones (5a, e, and f).The N-alkylanilides (