101975-23-9

Usage

Uses

3''-(Difluoromethoxy)acetophenone

Upstream product

• 121-71-1 3-Hydroxyacetophenone 
• 150542-06-6 α,α,α-iodinefluoroacetophenone 
• 98-86-2 acetophenone 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 75-45-6 Chlorodifluoromethane 

Downstream Products

• 443914-96-3 2-bromo-1-(3-difluoromethoxy-phenyl)ethanone 
• 926263-64-1 1-(3-difluoromethoxy-phenyl)-ethylamine 

Relevant academic research and scientific papers

Study on the mild, rapid and selective difluorocarbene-mediated triclassification of iododifluoroacetophenone with secondary amines and tree model for product classification

Difluorocarbene is a very active and widely used intermediate in organic synthesis. In this work, a room temperature difluorocarbene-mediated triclassification reaction of iododifluoroacetophenone (2) and secondary amines with mild condition, short reaction time (only 10 min) and high selectivity had been studied, which produced one of the following three substances: N-CF2H derivatives (up to 87% yield), formamides (82–89% yield) or the recycled starting secondary amines. This phenomenon was related to the structural stability of the corresponding products. If unstable, it would be hydrolyzed to formamides first, and then further hydrolyzed to starting amines. Based on the geometric structure of the raw materials, the corresponding prediction tree model was established, which provided guidance for the further application of difluoromethylation of Vemurafenib (1ee) and AZD9291 (1ff).

Catalytic radical difluoromethoxylation of arenes and heteroarenes

Intermolecular C-H difluoromethoxylation of (hetero)arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a redox-active difluoromethoxylating reagent 1a and photoredox catalysts for the direct C-H difluoromethoxylation of (hetero)arenes. Our approach is operationally simple, proceeds at room temperature, and uses bench-stable reagents. Its synthetic utility is highlighted by mild reaction conditions that tolerate a wide variety of functional groups and biorelevant molecules. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1a forming a neutral radical intermediate that liberates the OCF2H radical exclusively. Addition of this radical to (hetero)arenes gives difluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of difluoromethoxylation.

Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C?H Di- and Trifluoromethoxylation

Applications of TEMPO. catalysis for the development of redox-neutral transformations are rare. Reported here is the first TEMPO.-catalyzed, redox-neutral C?H di- and trifluoromethoxylation of (hetero)arenes. The reaction exhibits a broad substrate scope, has high functional-group tolerance, and can be employed for the late-stage functionalization of complex druglike molecules. Kinetic measurements, isolation and resubjection of catalytic intermediates, UV/Vis studies, and DFT calculations support the proposed oxidative TEMPO./TEMPO+ redox catalytic cycle. Mechanistic studies also suggest that Li2CO3 plays an important role in preventing catalyst deactivation. These findings will provide new insights into the design and development of novel reactions through redox-neutral TEMPO. catalysis.

DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME

The present invention provides a compound having the structure (I), a processing of making the compound; and a process of using the compound as a reagent for the difluoromethoxylation and trifluoromethoxylation of arenes or heteroarenes.

TETRAZOLINONE COMPOUND AND USE THEREOF

The compound represented by formula (1): wherein R4 and R5 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R6 represents a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or the like; R7, R8, and R9 each represents a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group, or the like; R13 represents a C1-C3 alkyl group, or the like; and Q represents a phenyl group, or the like; has an excellent control effect on pests.

SYNTHESIS OF DIFLUOROMETHYL ETHERS AND SULFIDES

The synthesis of difluoromethyl ethers and sulfides with a simple, non-ozone- depleting reagent is described. The difluoromethylation of phenols with this reagent occurs at room temperature within minutes with exceptional functional group tolerance. The mild conditions makes possible tandem processes for the conversion of aryl boronic acids, aryl halides and arenes to difluoromethyl ethers. Mechanistic studies support a reaction pathway involving nucleophilic attack of the phenolate to difluorocarbene.

Synthesis of benzylaminopyrimidines and their fungicidal activities against wheat brown rust and barley powdery mildew

Members of a new class of fungicide containing benzyl-aminopyrimidine as a core structure were synthesized and their fungicidal potencies against wheat brown rust, Puccinia recondita, and barley powdery mildew, Erysiphe graminis, were assessed. Among these fungicides, N-(fluoroalkoxy or fluorophenoxybenzyl)-4-pyrimidinamines showed notable preventive activities. The potency of the new pyrimidines was increased when a difluoromethoxy or tetrafluorophenoxy group was introduced at the 4- or 3-position of the phenyl moiety and a methyl or ethyl group was introduced at the benzyl position. Structure-activity relationships are discussed.