3070-40-4

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 1821-12-1 4-Phenylbutyric acid 

Downstream Products

• 120975-55-5 2-hydroxy-3-phenethyl-[1,4]naphthoquinone 
• 1083-56-3 1,4-diphenylbutane 
• 15719-64-9 methylammonium carbonate 
• 501-52-0 3-Phenylpropionic acid 
• 100-41-4 ethylbenzene 
• 60-12-8 2-phenylethanol 
• 28049-10-7 3-phenylpropionic acid 2-phenylethyl ester 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 100-42-5 styrene 
• 1064664-64-7 1-methyl-4-(4-phenylbut-1-yn-1-yl)benzene 
• 6305-31-3 2-(2-phenylethyl)-1,3-benzothiazole 
• 140244-00-4 1-fluoro-1,4-diphenylbutane 
• 65845-73-0 2-methyl-4-phenethylquinoline 

Relevant academic research and scientific papers

Development of BODIPY dyes with versatile functional groups at 3,5-positions from diacyl peroxides via Cu(ii)-catalyzed radical alkylation

An efficient Cu(ii)-catalyzed, C-H alkylation of BODIPY with a variety of alkyl diacyl peroxides has been developed for the first time, providing a late-stage and straightforward method for controllable synthesis of monoalkylated and dialkylated BODIPYs via a radical process that otherwise is difficult to obtain by literature methods. This chemo- and site-selective transformation will allow for the introduction of a variety of functionalities on the BODIPY core for highly versatile tethering to receptors and to other molecules of interest.

Decarboxylative C(sp3)?N cross-coupling of diacyl peroxides with nitrogen nucleophiles

We have disclosed a new radical-mediated decarboxylative C(sp3)?N cross-coupling of diacyl peroxides with nitrogen nucleophiles. The primary and secondary alkyl radicals derived from corresponding diacyl peroxides were generated by copper catalysis or by merging copper catalysis and photoredox catalysis, respectively. Various N-alkyl nitrogen nucleophiles, including indazoles, triazoles, indoles, purine, carbazole, anilines, and sulfonamide, were provided with a broad substrate scope and good functional group tolerance.

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Cu-Catalyzed Alkylarylation of Vinylarenes with Masked Alkyl Electrophiles

A Cu-catalyzed synthesis of a range of value-Added 1,1-diarylalkanes by radical alkylarylation of vinylarenes with alkyl peroxides as masked alkyl electrophiles is reported. The reaction features broad substrate scope, good functional group tolerance, and mild reaction conditions. Various bioactive molecules and key pharmaceutical intermediates have been easily synthesized by this method, demonstrating its synthetic value.

Radical alkylation of C(sp3)-H bonds with diacyl peroxides under catalyst-free conditions

Herein, we describe a protocol for alkylation reactions of C(sp3)-H bonds with diacyl peroxides by means of a process involving cross-coupling between an alkyl radical and an α-Aminoalkyl radical. The mild, catalyst-And additive-free conditions make this protocol superior to previously reported C(sp3)-H alkylation strategies. The protocol was applied to 1,2,3,4-Tetrahydroisoquinolines and a tetrahydro-β-carboline derivative and could be carried out on a gram scale, indicating its utility for the alkylation of late-stage synthetic intermediates.

Iron-Catalyzed Dehydrative Alkylation of Propargyl Alcohol with Alkyl Peroxides to Form Substituted 1,3-Enynes

This paper reports a new method for the generation of substituted 1,3-enynes, whose synthesis by other methods could be a challenge. The dehydrative decarboxylative cascade coupling reaction of propargyl alcohol with alkyl peroxides is enabled by an iron catalyst and alkylating reagents. Primary, secondary, and tertiary alkyl groups can be introduced into 1,3-enynes, affording various substituted 1,3-enynes in moderate to good yields. Mechanistic studies suggest the involvement of a radical-polar crossover pathway.

Iron(III)-Catalyzed Ortho-Preferred Radical Nucleophilic Alkylation of Electron-Deficient Arenes

The untraditional iron-catalyzed, ortho-preferred, radical alkylation of electron-deficient (hetero)arenes is reported. A variety of electron-deficient arenes were shown to react with various primary alkyl sources, producing the alkylated (hetero)arenes in good yields. This reaction might be an alkyl radical, nucleophilic aromatic substitution reaction, rather than the traditional electrophilic Friedel-Crafts reaction. HOMO-LUMO analysis and DFT studies on the key transition states underlying the regioselectivity are consistent with the observed reactions and the conclusions.

Copper-Catalyzed Decarboxylative Alkylation of Terminal Alkynes

A copper-catalyzed decarboxylative alkylation of terminal alkynes under mild reaction conditions has been reported. Various alkyl diacyl peroxides were applied as the alkyl source for the formation of C(sp3)?C(sp) bond. A range of terminal alkynes including aryl alkynes and alkyl alkynes delivered the alkylated internal alkynes with good to high performances. Mechanism studies suggested that this reaction involves a free radical pathway. (Figure presented.).

Iron-catalyzed C-H alkylation of heterocyclic C-H bonds

An efficient, iron-catalyzed C-H alkylation of benzothiazoles by using alkyl diacyl peroxides and alkyl tertbutyl peresters which are readily accessible from carboxylic acids to synthesize 2-alkylbenzothiazoles is developed. This reaction is environmentally benign and compatible with a broad range of functional groups. Various primary, secondary, and tertiary alkyl groups can be efficiently incorporated into diverse benzothiazoles. The effectiveness of this method is illustrated by late-stage functionalization of biologically active heterocycles.

Copper-catalyzed regioselective 1,2-alkylesterification of dienes to allylic esters

Copper catalyzed 1,2-alkylesterification of 1,3-dienes with diacyl peroxides affords branched allylic esters in excellent regioselectivity, including products with a newly generated fully substituted carbon center. The only byproduct is CO2. The reaction proceeds by a radical mechanism as suggested by spin trap and crossover experiments.