20396-49-0

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 3141-58-0 tert-butoxy radical 
• 3198-23-0 cyclohexane carboxylate 
• 105-07-7 4-cyanobenzaldehyde 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 192189-54-1 cis-4-phthaloylaminocyclohexanecarboxylic acid methyl ester 
• 89482-40-6 2-cyclohexyloxy-1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindole 
• 79650-21-8 α-cyclohexyl-p-methylacetophenone 
• 18869-27-7 (E)-(2-cyclohexylvinyl)benzene 
• 40115-03-5 2-cyclohexyl-benzothiazole 

Relevant academic research and scientific papers

FeCl2-Catalyzed Decarboxylative Radical Alkylation/Cyclization of Cinnamamides: Access to Dihydroquinolinone and Pyrrolo[1,2- a]indole Analogues

A simple and unified method for the synthesis of alkylated dihydroquinolinone and pyrrolo[1,2-a]indole derivatives in moderate to high yields (up to 91%) with excellent diastereoselectivity (>20:1 dr) was developed. The inexpensive FeCl2·4H2O works as catalyst, and easily prepared peresters (or peroxides) from aliphatic acids act as alkylating reagents and single electron oxidants. This environmentally friendly reaction proceeds via an FeCl2-catalyzed alkyl radical cascade addition/cyclization fashion.

Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters

Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-branched aliphatic carboxylic acids, which proceeds through the decarboxylation of the peresters and the subsequent formation of alkyl radicals to produce the alkylated adducts with an excellent diastereoselectivity. Theoretical calculations account for the observed reactivity and the outstanding stereocontrol. Importantly, the resultant compounds can be easily converted into ligands for asymmetric and catalytic transformations.

Iron-Catalyzed Vinylic C?H Alkylation with Alkyl Peroxides

A variety of alkyl peresters and alkyl diacyl peroxides, which are readily accessible from carboxylic acids, are utilized as general primary, secondary, and tertiary alkylating reagents for iron-catalyzed vinylic C?H alkylation of vinyl arenes, dienes, and 1,3-enynes. This transformation affords olefinic products in up to 98 % yield with high E/Z values. A broad range of functionalities, including carboxyl, boronic acid, methoxy, ester, amino, and halides, are tolerated. This protocol provides a facile approach to some olefins that are difficult to access, and hence, offers an alternative to existing systems. The synthetic utility of this method is demonstrated by late-stage functionalization of selected natural-product derivatives.

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-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides

An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C?C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed.

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.

Synthesis of tert-butyl peresters from aldehydes by Bu4NI- catalyzed metal-free oxidation and its combination with the Kharasch-Sosnovsky reaction

A new tert-butyl peresters synthesis directly from aldehydes and TBHP was developed via Bu4NI-catalyzed aldehyde C-H oxidation. Mechanistic studies suggest that the protocol proceeds via a radical process. Combining the method with the Kharasch-Sosnovsky reaction offers a practical approach for the synthesis of allylic esters from simple aldehydes and alkenes via a two-step one-pot procedure.