51315-70-9

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 6872-06-6 2-methyl indoline 
• 953395-19-2 (+/-)-1-[2-(4-methylphenylsulfonamido)phenyl]-2-propanyl 4-pentynoate 
• 51315-69-6 N-tosyl-o-allylaniline 

Downstream Products

• 95-20-5 2-methyl-1H-indole 
• 6872-06-6 2-methyl indoline 

Relevant academic research and scientific papers

Synthesis method for preparing 2-methylpyrrolidine compound through catalytic hydroamination reaction

The invention discloses a synthetic method for preparing a 2-methylpyrrolidine compound by catalyzing a hydroamination reaction, which comprises the following steps: A, sequentially adding a compound1, KI and KHSO4 into a reactor under an open condition;

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer

Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.

On the understanding of BF3·Et2O-promoted intra- and intermolecular amination and oxygenation of unfunctionalized olefins

BF3·Et2O was found to be effective for both intra- and intermolecular amination and oxygenation of unfunctionalized olefins. In the presence of 3 equiv. of BF3·Et2O, intramolecular hydroamination of N-(pent-4-enyl)-p-toluenesulfonamides, N-(hex-5-enyl)-p-toluenesulfonamides, intermolecular hydroamination between sulfonamides and cyclohexene, norbornene or styrene, lactonization of pent-4-enoic acid or hex-5-enoic acid compounds and esterification of cyclohexene with different carboxylic acids all proceeded readily, leading to the corresponding amination or oxygenation products in up to 99% isolated yields. Preliminary NMR experiments and DFT calculations suggested that the intramolecular hydroamination reactions proceeded via a sulfonimidic acid intermediate (N=S-OH), and formation of the corresponding Bronsted acid HF or HBF4 was less likely.

A novel organic electron donor derived from N-methylisatin

We report the reactivity of an electron donor derived from N-methylisatin on reduction by sodium amalgam. Transfer of a clear supernatant solution to iodoarenes affords the products of two-electron reduction. Reductions of sulfones, activated arenesulfonamides, and Weinreb amides are also reported.

Catalytic activation of the leaving group in the SN2 reaction

A novel catalytic activation of the leaving group in the SN2 reaction is achieved as an extension of our mercuric triflate-catalyzed reactions. Derivatives of anilinoethyl 4-pentynoate reacted smoothly with catalytic amounts of Hg(OTf)2 to give indoline derivatives in excellent yield with efficient catalytic turnovers under very mild conditions. The reaction of optically pure secondary alcohol derivatives resulted in inversion of stereochemistry, which is a definitive feature of the S N2 reaction. The procedure is applicable for benzoazepine synthesis.

Heptadecafluorooctanesulfonic acid (C8F17SO3H) catalyzed intramolecular hydroamination of olefinic sulfonamides in fluorous biphase system (FBS)

A practical, efficient, and environmentally benign intramolecular hydroamination of olefinic sulfonamides was carried out in fluorous biphase system (FBS) using commercially available heptadecafluorooctanesulfonic acid (C8F17SO3

Ruthenium-catalyzed intramolecular cyclization of hetero-functionalized allylbenzenes

Intramolecular addition of heterofunctionalities to C{double bond, long}C double bonds without β-hydride elimination was investigated and catalyzed by ruthenium complexes. The combination of RuCl3 · nH2O (10 mol%) and 3 equiv. of AgOTf acted as a catalyst for cyclization of 2-allylphenol (1a) to 2,3-dihydro-2-methylbenzofuran (2a) in good yield in the presence of Cu(OTf)2 as a co-catalyst and PPh3 as a ligand. This catalyst system also catalyzed the cyclization of 2-allylbenzoic acid to lactone in 91% yield. Then, a new catalyst system (RuCp*Cl2)2 (1.0 mol%)/4AgOTf/4PPh3, was found to be more active even in the absence of Cu(OTf)2. Furthermore, this catalysis was applied to asymmetric reaction of 2-allylphenol (1a). When using TolBINAP as a ligand, over 60% e.e. was achieved.

Intramolecular cyclization of phenol derivatives with C{double bond, long}C double bond in a side chain

Intramolecular cyclization of phenol derivatives with C{double bond, long}C double bond on a side chain was examined using copper and silver catalyst. For example, 2-allylphenol (1a) was converted to 2,3-dihydro-2-methylbenzofuran (2a) in 70% yield using Cu(OTf)2 or in 90% yield using AgClO4. This catalysis was applied to cyclization of 2-allylphenol derivatives, 2-(3-butenyl)phenol, benzoic acids with C{double bond, long}C double bond, 2-allyl-N-tosylaniline, and 2-(3-butenyloxy)phenol. Furthermore, allyl phenyl ether was converted to 2a via Claisen rearrangement and cyclization.

Phosphine gold(I)-catalyzed hydroamination of alkenes under thermal and microwave-assisted conditions

Phosphine gold(I) complexes catalyzed isomerization of terminal alkenes and hydroamination of unactivated alkenes under thermal and microwave-assisted conditions. This is the first example of the use of microwave radiation as a heat source for gold(I)-catalyzed organic reactions.

Synthesis of indolines and quinoline Via cyclization of N-arylsulfonyl-2-allylanilines catalyzed by bronsted acid

N-Arylsulfonyl-2-allylanilines underwent the intramolecular hydroamination to produce indolines or quinoline in the presence of catalytic amount of triflic acid with good yield. The scope of the reaction was extended to other N-protected aminoalkenes.