145838-86-4

Upstream product

• 591-50-4 iodobenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 108-59-8 malonic acid dimethyl ester 
• 67-56-1 methanol 
• 105-53-3 diethyl malonate 

Downstream Products

• 86001-89-0 triphenylarsonium bis(methoxycarbonyl)methylide 
• 118163-37-4 phenyliodoniomethanesulfonate 
• 82545-15-1 dimethyl 3-phenyloxirane-2,2-dicarboxylate 
• 3709-20-4 dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate 
• 72174-92-6 dimethyl 2,2-diphenyl-1,1-cyclopropanedicarboxylate 
• 1190202-68-6 C₂₅H₃₅NO₇Si 
• 1190202-46-0 C₂₂H₁₉NO₆ 
• 1190202-62-0 C₁₆H₁₆N₂O₈S 
• 1190202-64-2 C₁₈H₂₀N₂O₈S 
• 1190202-67-5 C₂₄H₂₃NO₆ 
• 1190202-63-1 C₁₇H₁₈N₂O₈S 
• 1190202-50-6 C₂₁H₂₄N₂O₈S 
• 1206604-34-3 dimethyl 2-(3,3-diphenyl-3-(trimethylsilyl)prop-1-ynyl)cyclopropane-1,1-dicarboxylate 
• 1206604-32-1 dimethyl 2-(4-phenylbut-1-yn-1-yl)cyclopropane-1,1-dicarboxylate 

Relevant academic research and scientific papers

All-Carbon Tetrasubstituted Olefins Synthesis from Diazo Compounds and Iodonium Ylides under Blue LED Irradiation

A route for the construction of all-carbon tetra-substituted olefins through visible-light promoted coupling of diazo compounds with iodonium ylides was developed. A wide range of all-carbon tetra-substituted olefins was obtained in moderate to good yields. The synthetic values of the current method were further approved by the synthesis of natural isolates modified alkenes and the successful transformation of final olefins into important heterocycles. (Figure presented.).

Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?

An anodic oxidation enabled synthesis of hypervalent iodine(III) reagents from aryl iodides is demonstrated. Under mild electrochemical conditions, a range of aryliodine(III) reagents including iodosylarenes, (difunctionaliodo)arenes, benziodoxoles and diaryliodonium salts can be efficiently synthesized and derivatized in good to excellent yields with high selectivity. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner avoiding the use of expensive or hazardous chemical oxidants.

A sustainable C-H functionalization of indoles, pyrroles and furans under a blue LED with iodonium ylides

Pyrrole and indole derivatives are functionalizedviaa green initiative with the dimethyl malonate derived phenyl iodonium ylide4ain the presence of a blue LEDviaC-H functionalization of the respective heterocycles in methanol to generate the desired compounds5-7in moderate to good yields. Control experiments provide insight into the probable reaction mechanism. Finally, the strategy is successfully applied in the generation of azepino[4,5-b]indole12a/b.

Blue LED Irradiation of Iodonium Ylides Gives Diradical Intermediates for Efficient Metal-free Cyclopropanation with Alkenes

A facile and highly chemoselective synthesis of doubly activated cyclopropanes is reported where mixtures of alkenes and β-dicarbonyl-derived iodonium ylides are irradiated with light from blue LEDs. This metal-free synthesis gives cyclopropanes in yields

Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation

A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.

Palladium-Catalyzed Dehydrogenation Coupling-Cyclization Reactions of Acetylenic Acids with Iodonium Ylides for the Synthesis of 2(5 H)-Furanones

A new route for the synthesis of 2(5H)-furanones is presented via Pd(PPh3)4-catalyzed cascade reaction of acetlenic acids with iodonium ylides using K2CO3 as the base. The cascade proceeds through dehydrogenatio

Continuous Processing and Efficient in Situ Reaction Monitoring of a Hypervalent Iodine(III) Mediated Cyclopropanation Using Benchtop NMR Spectroscopy

Real-time NMR spectroscopy has proven to be a rapid and an effective monitoring tool to study the hypervalent iodine(III) mediated cyclopropanation. With the ever increasing number of new synthetic methods for carbon-carbon bond formation, the NMR in situ monitoring of reactions is becoming a highly desirable enabling method. In this study, we have demonstrated the versatility of benchtop NMR using inline and online real-time monitoring methods to access mutually complementary information for process understanding, and we developed new approaches for real-time monitoring addressing challenges associated with better integration into continuous processes.

Sc(OTf)3-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Phthalazinium Dicyanomethanides

The Sc(OTf)3-catalyzed diastereoselective [3 + 3] cycloaddition of phthalazinium dicyanomethanides with cyclopropane 1,1-diesters proceeded smoothly under mild reaction conditions, affording a variety of 3,4-dihydro-1H-pyrido[2,1-a]phthalazine derivatives in up to 99% yields with excellent diastereoselectivities.

Gold-Catalyzed Rearrangement of Alkynyl Donor-Acceptor Cyclopropanes to Construct Highly Functionalized Alkylidenecyclopentenes

A gold-catalyzed 1,7-addition-cyclization-elimination cascade sequence performed on a range of alkynyl-substituted donor-acceptor-type cyclopropanes provides facile entry to highly functionalized exo-alkylidenecyclopentenes under very mild conditions. Iso

Transition-metal-free approach to synthesis of indolines from N-(ortho-chloromethyl)aryl amides and iodonium ylides

A transition-metal-free method for the synthesis of indolines has been developed. In the presence of K2CO3, the cyclization reaction of N-(ortho-chloromethyl)aryl amides and iodonium ylides proceeded smoothly at room temperature in moderate to good yields.