442850-92-2

Upstream product

• 78839-75-5 2-bromo-N-(tert-butoxycarbonyl)aniline 
• 92988-08-4 trivinylboroxin 
• 27326-43-8 2-vinylbenzoic acid 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3867-18-3 2-vinylaniline 
• 4248-19-5 tert-butyl carbazate 
• 105952-36-1 1-iodo-2-(2-iodoethyl)-benzene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 615-36-1 2-bromoaniline 
• 5339-85-5 2-aminophenethyl alcohol 
• 880384-47-4 di-tert-butyl (2-bromophenyl)carbamate 

Downstream Products

• 686775-90-6 tert-butyl benzyl(2-vinylphenyl)carbamate 
• 894810-56-1 allyl-(2-vinyl-phenyl)-carbamic acid tert-butyl ester 
• 686776-03-4 tert-butyl (4-methylphenyl)sulfonyl(2-vinylphenyl)carbamate 
• 34943-91-4 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one 

Relevant academic research and scientific papers

Ruthenium Amide Complexes – Synthesis and Catalytic Activity in Olefin Metathesis and in Ring-Opening Polymerisation

A set of olefin metathesis catalysts bearing a ruthenium amide moiety was synthesised. In the ruthenium amide form these complexes exhibit very low activity in standard metathesis reactions. However, a dramatic increase of activity was observed upon in si

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Thiol-ene/oxidation tandem reaction under visible light photocatalysis: Synthesis of alkyl sulfoxides

The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y. This is a metal-free method which uses a low catalyst loading, atmospheric oxygen as the oxidant, and visible light conditions (green light). A mechanism has been proposed that is consistent with the experimental results.

Ruthenium-amido complexes: Synthesis, structure, and catalytic activity in olefin metathesis

Unprecedented amido derivatives of the first-, second-, and third-generation Grubbs ruthenium catalysts were prepared, characterized, and tested in ring-closing metathesis (RCM) of model dienes. In the ruthenium-amide (formally: 2-ruthenaindole) form, the

Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction

(Chemical Equation Presented) A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.

Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles

A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.

Indole synthesis by controlled carbolithiation of o-aminostyrenes

An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

Construction of nitrogen-heterocyclic compounds through zirconium mediated intramolecular alkene-carbonyl coupling reaction of N-(o-alkenylaryl)carbamate derivatives

Intramolecular alkene-carbonyl coupling reaction of N-benzyl-N-(o- alkenylaryl)carbamate derivative derived from o-aminostyrene, o-(aminomethyl)styrene and o-aminoallylbenzene smoothly proceeded by treating with zirconocene-butene complex to give the corresponding lactam derivative.

New organolithium addition methodology to diversely functionalized indoles

A novel synthetic approach to diversely functionalized indoles is described. Boc-protected ortho-aminostyrenes undergo an alkyllithium addition reaction, thereby generating a lithiated intermediate, which upon reaction with specific electrophiles sets up

Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane

The synthesis of functionalized styrene derivatives can be readily achieved utilizing a Suzuki cross-coupling protocol between aryl halides and 2,4,6-trivinylcyclotriboroxane-pyridine complex. The scope and limitations of the procedure were demonstrated by investigation of an array of ortho-substituted aryl halides.