78811-32-2

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 626-62-0 Cyclohexyl iodide 
• 24371-94-6 cyclohexylmercury chloride 
• 110-82-7 cyclohexane 
• 119-65-3 isoquinoline 
• 2043-61-0 cyclohexanecarbaldehyde 
• 5281-18-5 benzaldehyde, hydrazone 
• 108-85-0 1-bromocyclohexane 
• 615-22-5 2-methylmercaptobenzothiazole 

Relevant academic research and scientific papers

Ni-Catalyzed Reductive Liebeskind-Srogl Alkylation of Heterocycles

Herein we present a Ni-catalyzed alkylation of C-SMe with alkyl bromides for the decoration of heterocyclic frameworks. The protocol, reminiscent to the Liebeskind-Srogl coupling, makes use of simple C(sp2)-SMe to be engaged in a reductive coupling. The reaction is suitable for a preponderance of highly valuable heterocyclic motifs. In addition to cyclic bromides, noncyclic alkyl bromides are well accommodated with exquisite levels of retention over isomerization. The protocol is scalable and permits orthogonal couplings in the presence of other functionalization handles.

Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides

An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Substituted Hantzsch Esters as Versatile Radical Reservoirs in Photoredox Reactions

Substituted Hantzsch esters can act as radical reservoirs in photoredox reactions, steadily releasing a carbon radical and a hydrogen atom radical in the absence of an additional electron acceptor. We propose that radical release by substituted Hantzsch esters occurs via a mechanism involving an internal redox cycle. Cinnamidecinnamides, styrenes, α,β-unsaturated acids, and diarylethenes could be alkylated smoothly with these reagents. (Figure presented.).

Nickel-catalyzed selective oxidative radical cross-coupling: An effective strategy for inert Csp3-H functionalization

An effective strategy for inert Csp3-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated. Density functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments. Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp3-H arylation products in good yields.

Metal-Free Oxidative Decarbonylative Coupling of Aliphatic Aldehydes with Azaarenes: Successful Minisci-Type Alkylation of Various Heterocycles

A metal-free oxidative decarbonylative coupling of aliphatic aldehydes with various electron-deficient heterocycles has been developed. This reaction is supposed to be realized via a Minisci-type mechanism, based on the substrate scope, regioselectivity and radical trapping experiments. The ready availability of aliphatic aldehydes, metal-free conditions and broad substrate scope should make this method attractive for the late-stage alkylation of bioactive heterocycles.

Dimeric Metal Complexes as Mediator for Radical C-C Bond-Forming Reactions

Irradiation of dicarbonyl(η5-cyclopentadienyl)iron dimer 1 or decacarbonyldimanganese (2) in the presence of alkyl halides leads to C-centered radicals which can be trapped by alkenes and yields saturated and/or unsaturated addition products.Carbon radicals are generated via halogen abstraction by the initially formed metal-centered radicals resulting from homolysis of the metal-metal bond of dimeric mediators 1 and 2.No reaction occurs using octacarbonyl dicobalt (3).

GENERATION AND SYNTHETIC USE OF ALKYL RADICALS WITH 2 AS MEDIATOR

Irradiation of dimeric iron complex 1 in the presence of alkyl halides yields alkyl radicals that are useful in organic synthesis.

Polar Substituent Effects in Additions of Alkyl Radicals to Alkenes

Reduction of cyclohexylmercuric salts (7) with NaBH4 yields cyclohexyl radicals (8).Their rel. rates of addition to substituted styrenes 4, acrylic esters 5 and acrylonitriles 6 have been measured.Comparison with Hammett ?-values shows, that substituents at the non attacked vinylic carbon atom show polar effects mainly (Table 1).The effect of a substituent variation increases with increase of the reactivity of the alkenes (Table 2).Mesomeric and steric effects play only a minor role.