91083-83-9

Upstream product

• 14352-61-5 methyl cyclohexylacetate 
• 5452-75-5 ethyl 2-cyclohexylacetate 
• 530-48-3 1,1-Diphenylethylene 
• 626-62-0 Cyclohexyl iodide 
• 119-61-9 benzophenone 
• 1088-01-3 tricyclohexylborane 
• 26189-62-8 phenyl 2,2-diphenylethenyl sulfone 
• 24522-19-8 Ph₂CCHHgCl 
• 67341-86-0 Ph₂CCHHgBr 
• 110-82-7 cyclohexane 
• 5670-69-9 1,1'-(2-nitroethene-1,1-diyl)dibenzene 
• 19997-66-1 1-iodo-2,2-diphenylethylene 
• 24371-94-6 cyclohexylmercury chloride 
• 22072-53-3 Ph₂CCHMgBr 

Downstream Products

• 119-61-9 benzophenone 
• 98-89-5 Cyclohexanecarboxylic acid 

Relevant academic research and scientific papers

Visible-Light-Mediated C-I Difluoroallylation with an α-Aminoalkyl Radical as a Mediator

Herein, we report a protocol for direct visible-light-mediated C-I difluoroallylation reactions of α-trifluoromethyl arylalkenes with alkyl iodides at room temperature with an α-aminoalkyl radical as a mediator. The protocol permits efficient functionalization of various α-trifluoromethyl arylalkenes with cyclic and acyclic primary, secondary, and tertiary alkyl iodides and is scalable to the gram level. This mild protocol uses an inexpensive mediator and is suitable for late-stage functionalization of complex natural products and drugs.

Tandem vinyl radical Minisci-type annulation on pyridines: one-pot expeditious access to azaindenones

A new regiospecific alkylative/alkenylative cascade annulation of pyridines has been achieved whilst the corresponding classic Minisci alkylative annulation failed. This protocol provides a novel and expeditious access to azaindenones and related compoundsviacross-dehydrogenative coupling with the long-standing problem of C2/C4 regioselectivity of pyridines being well addressed.

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.

Cross-Dehydrogenative Coupling of Strong C(sp3)-H with N-Heteroarenes through Visible-Light-Induced Energy Transfer

The sustainable cross-dehydrogenative coupling of strong C(sp3)-H with N-heteroarenes has been developed using an efficient organic photocatalyst. It features atomic- and step-economy, and acid-free conditions. Mechanism studies suggest a previous elusive

Alkenylation of unactivated alkyl bromides through visible light photocatalysis

Two visible-light driven alkenylation reactions of unactivated alkyl bromides, which were enabled by the use of Ir(dF(CF3)ppy)2(dtbbpy)PF6 as the photocatalyst and (TMS)3SiH as the atom transfer reagent to activate the alkyl bromides, were described for the first time. These protocols can be used to produce a variety of alkenes from easily available feedstock with good reaction efficiency and high chemoselectivity under mild reaction conditions. To further demonstrate the applicability of the present strategy, the alkenylation of bioactive molecules and glycosyl bromides, as well as the alkynylation of unactivated alkyl bromides, was proven to be feasible.

Oxidative Addition to Palladium(0) Made Easy through Photoexcited-State Metal Catalysis: Experiment and Computation

Visible-light induced, palladium catalyzed alkylations of α,β-unsaturated acids with unactivated alkyl bromides are described. A variety of primary, secondary, and tertiary alkyl bromides are activated by the photoexcited palladium metal catalyst to provide a series of olefins at room temperature under mild reaction conditions. Mechanistic investigations and density functional theory (DFT) studies suggest that a photoinduced inner-sphere mechanism is operative in which a barrierless, single-electron transfer oxidative addition of the alkyl halide to Pd0 is key for the efficient transformation.

Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow

Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.

Visible Light-Induced Regioselective Decarboxylative Alkylation of the C(sp2)?H Bonds of Non-Aromatic Heterocycles

With sunlight or blue LEDs irradiation, regioselective decarboxylative alkylation of various non-aromatic heterocycles has been realized via C(sp3)-centered radical C(sp2)?C(sp3) bond formation under oxidant-free condition

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.