52850-98-3

Upstream product

• 4514-04-9 7,8,9,10-tetrahydro-6(5H)-phenanthridinone 
• 74-88-4 methyl iodide 
• 552857-08-6 2-bromo-N-methyl-N-phenyl-1-cyclohexene-1-carboxamide 
• 68965-62-8 2-bromocyclohex-1-enecarboxylic acid 
• 72422-64-1 2-bromocyclohex-1-ene-1-carboxylic acid methyl ester 
• 552857-10-0 2-bromo-N-phenyl-1-cyclohexene-1-carboxamide 
• 6832-87-7 2-bromo-N-methylaniline 
• 93493-95-9 2-{[(trifluoromethyl)sulfonyl]oxy}cyclohex-1-enecarboxylic acid methyl ester 
• 41302-34-5 2-(methoxycarbonyl)cyclohexanone 
• 348-54-9 2-Fluoroaniline 

Relevant academic research and scientific papers

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.

A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls

Tricyclic biaryls are important scaffold structures in many natural products and lead compounds in drug discovery. The formation of a biaryl unit is often the key step for the synthesis of tricyclic biaryls. Despite significant progress toward the synthesis of biaryl compounds in recent years, the direct cross-coupling of two different aryl halides is still challenging and robust methods are lacking. Herein we report a direct cross-coupling of two different aryl halides in the presence of a palladium catalyst and boron ester, which provides a new and useful complementary method to synthesize tricyclic biaryls.

Concise synthesis of tetrahydrophenanthridone by palladium reagent

Heck reaction of N-(2-halophenyl)-N-methyl-1-cyclohexene-1carboxamide (1) and 2-bromo-N-methyl-N-phenyl-1-cyclohexene-1-carboxamide (4) using a palladium reagent under several reaction conditions was examined. Reaction of 4 using Pd(OAc)2, DPPP, and Bu3P afforded tetrahydrophenanthridone (5) in excellent yield.