124985-23-5

Upstream product

• 83-33-0 inden-1-one 
• 100-46-9 benzylamine 

Downstream Products

• 124985-31-5 N-benzyl-N-(inden-1-yl)-2-iodobenzamide 
• 66399-68-6 (+)-N-Benzylindan-1-amine 
• 109270-61-3 C₂₃H₁₇NO 
• 66399-68-6 (+)-N-benzylindan-1-amine 

Relevant academic research and scientific papers

New Possibilities of the Kabachnik–Fields and Pudovik Reactions in the Phthalocyanine-Catalyzed Syntheses of α-Aminophosphonic and α-Aminophosphinic Acid Derivatives

The results of systematic studies demonstrated wide possibilities of the three-component Kabachnik–Fields and two-component Pudovik reactions catalyzed by metal phthalocyanines in the synthesis of structurally diverse α-aminophosphonates. Extension of this catalytic method to the synthesis α-aminophosphinates gave rise to a series of α-amino- and α-hydrazinophosphinates based on biogenic amino acids. A number of α-hydrazinophosphonates showed a good antioxidant activity.

A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin

The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compounds.

Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes

The synthesis and study of the catalytic activity of 1,2,4,3-triazaphospholenes (TAPs) is reported. TAPs represent a more modular scaffold than previously reported diazaphospholenes. TAP halides were shown to catalyze the 1,2 hydroboration of 19 imines, and three α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.

Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes

The first use of diazaphospholenes as chiral catalysts has been demonstrated with enantioselective imine hydroboration. A chiral diazaphospholene prepared in a simple three-step synthesis from commercial materials has been shown to achieve the highest enantioselectivity for the hydroboration of alkyl imines with pinacolborane reported to date. Enantiomer ratios of up to 88:12 were obtained with low (2 mol %) catalyst loadings. Twenty examples of asymmetric reduction employing this main-group catalysis protocol, including the synthesis of the pharmaceuticals ent-rasagiline and fendiline, are shown.

Synthesis and catalytic reactivity of bis(amino)cyclopropenylidene carbene-borane adducts

The first reported neutral boron(III) adducts of bis(amino)cyclopropenylidene carbenes (BAC carbenes) have been synthesized, structurally characterized, and applied in homogeneous reaction chemistry. These air-stable adducts have been prepared by the combination of a BAC carbene lithium tetrafluoroborate adduct with borane dimethyl sulfide, boron trifluoride etherate, or dicyclohexylborane. A borenium cation derived in situ from the dicyclohexylborane adduct catalytically reduces unhindered benzyl ketimines, a class of substrate that cannot be reduced by prior borenium catalysts, at room temperature, employing 20 atm of hydrogen gas as the terminal reductant.

Pd(OAc)2-catalyzed carbonylation of amines

A phosphine-free catalytic system [Pd(OAc)2-Cu(OAc) 2-air] induced a substrate-specific carbonylation of amines in boiling toluene under CO gas (1 atm). Symmetrical N,N′-dialkylureas were obtained by the carbonylation of primary amines. N,N,N′-Trialkylureas were selectively formed by addition of a secondary amine to the above reaction vessel. Secondary amines did not give tetraalkylureas. However, dialkylamines with a phenyl group on their alkyl chains, such as N-monoalkylated benzylic amine or phenethylamine derivatives, underwent a direct aromatic carbonylation to afford five- or six-membered benzolactams. In the carbonylation, the chelation effect or steric repulsion between Pd(II) and the meta-substituent in the ortho-palladation and the ring sizes of cyclopalladation products that were formed prior to carbonylation were found to generate good site selectivity and increase the reaction rate. In contrast, carbonylation of ω- arylalkylamines with a hydroxyl group gave neither ureas nor benzolactams but instead produced 1,3-oxazolidinones smoothly. Hydrochlorides of amines also underwent carbonylation to afford the corresponding amides under the conditions used. This procedure made it possible to prepare ureas of amino acid esters and N-alkylcarbamates in practical yields.