1454769-77-7

Basic information

• Product Name: C₁₁H₁₂INO
• Synonyms: C₁₁H₁₂INO
• CAS NO: 1454769-77-7
• Molecular Weight: 301.127
• Mol File: 1454769-77-7.mol

Chemical Properties

• CAS DataBase Reference: C₁₁H₁₂INO(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₁H₁₂INO(1454769-77-7)
• EPA Substance Registry System: C₁₁H₁₂INO(1454769-77-7)

Safety Data

• Hazardous Substances Data: 1454769-77-7(Hazardous Substances Data)

Upstream product

• 29289-13-2 2-iodo-4-methylaniline 
• 920-46-7 Methacryloyl chloride 

Downstream Products

• 1454770-01-4 (E)-1,3,5-trimethyl-3-styrylindolin-2-one 
• 1454769-78-8 N-(2-iodo-4-methylphenyl)-N-methylmethacrylamide 

Relevant articles and documents

Domino Carbopalladation/C-H Functionalization Sequence: An Expedient Synthesis of Bis-Heteroaryls through Transient Alkyl/Vinyl-Palladium Species Capture

A microwave-assisted highly efficient intermolecular domino carbopalladation/C-H functionalization sequence has been developed to access bis-heteroaryl frameworks in a single operation. The reaction involves carbopalladation of the halogenated acrylamides

Palladium-Catalyzed Enantioselective Intramolecular Heck Carbonylation Reactions: Asymmetric Synthesis of 2-Oxindole Ynones and Carboxylic Acids

Herein, we report a Pd-catalyzed enantioselective domino Heck carbonylation reaction of o-iodoacrylanilides with terminal alkynes and water as the nucleophiles, affording a diversity of β-carbonylated 2-oxindole derivatives bearing a 3,3-disubstituted all-carbon quaternary stereocenter, in high yields (55–99 %) with good to excellent enantioselectivities (up to 99 % ee). The synthetic utilities of the protocol were demonstrated in the gram-scale synthesis of 2-oxindole-derived ynone 3 ea and carboxylic acid 4 a, as well as the facile synthesis of chiral 2-oxindoles with a pyrazole or isoxazole moiety.

Palladium-Catalyzed Domino Synthesis of 2,3-Difunctionalized Indoles via Migratory Insertion of Isocyanides in Batch and Continuous Flow

We report, herein, a palladium-catalyzed cascade comprising carbopalladation, migratory insertion of isocyanide and triple bond activation followed by a nucleophilic attack (OR?) to construct difunctionalized acyl indoles. The process involves

Pd/Cu-Catalyzed Enantioselective Sequential Heck/Sonogashira Coupling: Asymmetric Synthesis of Oxindoles Containing Trifluoromethylated Quaternary Stereogenic Centers

An asymmetric palladium and copper co-catalyzed Heck/Sonogashira reaction between o-iodoacrylanilides and terminal alkynes to synthesize chiral oxindoles was developed. In particular, a wide range of CF3-substituted o-iodoacrylanilides reacted

3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes

Arylboration and arylsilylation reactions of N-(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (B2pin2) or PhMe2Si-Bpin are developed by using simple CuOAc as the sole catalyst. A range of boron-or silane-bearing 3,3′-disubstituted oxindoles are obtained in moderate to excellent yields. The reaction is proposed to proceed via a domino sequence involving intermolecular olefin borylcupration or silylcupration followed by intramolecular coupling of an alkyl-Cu intermediate with aryl iodide.

Nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy

Herein reported is a nickel-catalyzed reductive aryl thiocarbonylation of alkene via thioester group transfer strategy by using simple and readily available thioesters. In contrast to traditional activation of weaker C(acyl)-S bond, the C(acyl)-C bond of

Palladium-Catalyzed Domino Heck/Silylation Reaction for the Synthesis of (2-Oxoindolin-3-yl)methylsilanes via Trapping of the σ-Alkylpalladium Intermediates with Disilanes

A palladium-catalyzed domino Heck/silylation reaction of acrylamides with hexamethyldisilane is presented. This transformation, which involves the formation of a σ-alkylpalladium intermediate, allows direct access to functionalized (2-oxoindolin-3-yl)methylsilanes in good to excellent yields. Furthermore, this strategy could be utilized for the synthesis of (2-oxoindolin-3-yl)methylstannanes from hexamethyldistannane. (Figure presented.).

Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the σ-alkylpalladium intermediate with boron

Pd-catalyzed domino Heck/borylation of acrylamides with B2pin2 is reported to generate synthetically useful indolinone-3-methyl boronic esters, via capturing σ-alkyl palladium with boron. Further functionalization of the obtained boronic ester qualify it as a new starting point for the functionalization of specific C(sp3)-H bond. Moreover, the application of an Ugi-adduct as starting material or B2nep2 as an alternative boron source works equally well, making this a broadly applicable and robust method for the formation of a C-C and C-B bond in a single operation.

Pd-catalyzed Heck-type cascade reactions with N-tosyl hydrazones: An efficient way to alkenes via in situ generated alkylpalladium

A palladium-catalyzed Heck-type cascade reaction of aryl halides and N-tosyl hydrazones is reported. The neopentylpalladium species, generated from an intramolecular Heck-type insertion reaction of aryl halides, could efficiently react with carbenes to fo