86396-02-3

Basic information

• Product Name: Iodonium, phenyl-, 2,6-dioxocyclohexylide
• CAS NO: 86396-02-3
• Molecular Formula: C12H11IO2
• Molecular Weight: 314.123
• Mol File: 86396-02-3.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Iodonium, phenyl-, 2,6-dioxocyclohexylide(CAS DataBase Reference)
• NIST Chemistry Reference: Iodonium, phenyl-, 2,6-dioxocyclohexylide(86396-02-3)
• EPA Substance Registry System: Iodonium, phenyl-, 2,6-dioxocyclohexylide(86396-02-3)

Safety Data

• Hazardous Substances Data: 86396-02-3(Hazardous Substances Data)

Upstream product

• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 504-02-9 1,3-cylohexanedione 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 536-80-1 iodosylbenzene 
• 591-50-4 iodobenzene 
• 1460-08-8 2-diazocyclohexane-1,3-dione 

Downstream Products

• 82584-78-9 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid methyl ester 
• 127724-12-3 4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid methyl ester 
• 201024-63-7 2-methyl-4,5,6,7-tetrahydro-1,3-benzoxazol-4-one 
• 121692-45-3 4-oxo-4,5,6,7-tetrahydro-1,3-benzoxathiole-2-thione 
• 92898-23-2 2-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-one 
• 4322-62-7 cyclohexane-1,2,3-trione 
• 52252-82-1 5-benzyl-3,4-dihydrophenanthridine-1,6(2H,5H)-dione 

Relevant articles and documents

Rh(III)-Catalyzed Chemodivergent Annulations between Indoles and Iodonium Carbenes: A Rapid Access to Tricyclic and Tetracyclic N-Heterocylces

Herein, we report an acid-controlled highly tunable selectivity of Rh(III)-catalyzed [4 + 2] and [3 + 3] annulations of N-carboxamide indoles with iodonium ylides lead to form synthetically important tricyclic and tetracyclic N-heterocycles. Here, iodonium ylide serves as a carbene precursor. The protocol proceeds under operationally simple conditions and provides novel tricyclic and tetracyclic scaffolds such as 3,4-dihydroindolo[1,2-c]quinazoline-1,6(2H,5H)-dione and 1H-[1,3]oxazino[3,4-a]indol-1-one derivatives with a broad range of functional group tolerance and moderate to excellent yields. Furthermore, the protocol synthetic utility was extended for various chemical transformations and was easily scaled up to a large-scale level.

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

Support-Free Pd3Co NCs as an Efficient Heterogeneous Nanocatalyst for New Organic Transformations of C?C Coupling Reactions

A support-free heterogeneous Pd3Co nanostructured composite (NC), synthesized through a hydrothermal route, acted as an effective catalytic system in multivariate Heck-, Sonogashira-, and Suzuki-type coupling reactions of iodonium ylides. The XPS analysis of the bimetallic Pd3Co NCs confirmed the elemental composition as 75 % palladium and 25 % cobalt. Furthermore, high-resolution (HR) TEM analysis confirmed the spherical morphology of the Pd3Co bimetallic nanoparticles. The average diameter of the NCs is 14.8 nm. The coupling reaction proceeded through the generation of α-iodoenones with simultaneous migration of the phenyl group, thereby giving a scaffold with higher atom economy. The heterogeneous Pd3Co NCs were recycled and reused without any significant change in catalytic ability for up to five reaction cycles. The high concentration of Pd and association of cobalt into the lattice of palladium appears to enhance its catalytic ability for the diverse coupling reactions in comparison with its monometallic counterparts as well as with bimetallic NCs with a comparatively lesser amount of Pd.