84904-06-3

Upstream product

• 627-27-0 homoalylic alcohol 
• 100-07-2 4-methoxy-benzoyl chloride 
• 201230-82-2 carbon monoxide 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 100-09-4 4-methoxybenzoic acid 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Downstream Products

• 84904-10-9 3-nitrato-4-piperidinobutyl-p-methoxylbenzoate 
• 84904-14-3 3-hydroxy-4-piperidinobutyl-p-methoxylbenzoate 

Relevant academic research and scientific papers

Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols

An alcohol-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents is reported. This transformation is enabled by specifically tailored O-(2,6-dimethoxybenzoyl)hydroxylamine electrophiles that suppress competitive processes, including undesired β-hydride elimination and transesterification between the alcohol substrate and electrophile. The reaction delivers the desired 1,2-carboaminated products with generally high regio- and syn-diastereoselectivity and exhibits a broad scope of coupling partners and alkenes, including complex natural products. Various mechanistic experiments and analysis of the stereochemical outcome with a cyclic alkene substrate, as confirmed by X-ray crystallographic analysis, support alcohol-directed syn-insertion of an organonickel(I) species.

Bromotrifluoromethane: A Useful Reagent for Hydrotrifluoromethylation of Alkenes and Alkynes

Bromotrifluoromethane (CF 3 Br) is a simple, inexpensive and abundant industrial material employed as a trifluoromethylating reagent. However, only limited strategies using CF 3 Br as a fluorine source are reported. Herein, we describe a visible-light-induced hydrotrifluoromethylation of alkenes and alkynes with CF 3 Br. The reaction proceeds under mild conditions with good functional group tolerance, providing a new route for the application of BrCF 3 in organic synthesis.

Metal-free, room-temperature, radical alkoxycarbonylation of aryldiazonium salts through visible-light photoredox catalysis

The first radical alkoxycarboxylation of aryldiazonium salts using CO gas through visible-light-induced photoredox catalysis (16 W blue LEDs) has been developed. This reaction is entirely metal-free, is carried out at room temperature with a low loading of an organic dye as a photocatalyst (0.5 mol%), and provides a wide range of arylcarboxylic acid esters in high yields. Importantly, this photocatalytic system can be successfully extended to other carboxylation reactions.

Nitrosamine Photolysis as a Synthetic Method: The Addition of Aminium Radicals to Unsaturated Carbon-Carbon Bonds

Acid complexed nitrosamines decompose from their lowest singlet excited state to gine aminium radicals and nitric oxide radical transients.Aminium radicals initiate addition of various unsaturated groups to give 1-amino-2-nitroso compounds under an inert atmosphere, or 1-amino-2-nitrates under oxygen.In this report, photoaddition of nitroamines to olefins, acetylenes and fused aromatic hydrocarbons, and the subsequent transformations of the intermediates are described.Aminium radical initiated intramolecular cyclization to prepare tetracyclic aza compounds is also described.While photoaddition of nitrosamines to 4-propenylanisole or 3-butenol wes efficient, that to 3-butenyl benzoates under oxidative conditions was only fair, obviously due to the presence of a benzene ring.The oxidative photoaddition to 3-butenyl halide was followed by spontaneous cyclization to an azaspiro compound.The photoaddition to phenyl-substituted acetylenes gave β-nitroso enamines which hydrolyzed to diketomonoximes under neitral conditions but decomposed extensively under acidic conditions.Certain fused aromatic hydrocarbons acted as singlet sensitizers as well as substrates to induce similar addition giving amino nitroso adducts.These adducts took different courses of conversion dependent on reaction conditions, and on steric and electronic factors.