24028-79-3

Upstream product

• 6971-51-3 3-methoxybenzyl alcohol 
• 104-94-9 4-methoxy-aniline 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 15144-80-6 N,N-diethyl-4-methoxyaniline 
• 120455-06-3 5-methoxy-2-(4-methoxyphenyl)-2H-indazole 

Relevant academic research and scientific papers

Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles

The cross-coupling of C-N bond directly from inert C-H bonds is an ideal approach to synthesize saturated azacycles due to its high efficiency and atom economy. In this article, a copper-catalyzed intramolecular amination via the cross coupling of C(sp3)-H and N-H bonds of secondary amine has been reported, which exhibit excellent chemo- and regioselectivity, extensive substrate scope, and functional group tolerance in good to excellent yield, offering an efficient pathway to build nitrogen-containing heterocycle skeletons.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

Tert-Butyl Hydroperoxide-Mediated Oxo-Sulfonylation of 2 H-Indazoles with Sulfinic Acid toward Indazol-3(2 H)-ones

A new and efficient oxo-sulfonylation protocol has been established for the synthesis of N-sulfonylated indazolones employing sulfinic acid as a sulfonylating agent using tert-butyl hydroperoxide (TBHP) under ambient air. A series of structurally diverse 1-sulfonylindazol-3(2H)-one derivatives were obtained in good yields. A radical reaction mechanism has been proposed for this transformation.

Ni-Catalyzed asymmetric reduction of α-keto-β-lactams: via DKR enabled by proton shuttling

Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed asymmetric hydrogenation, providing the corresponding α-hydroxy-β-lactam derivatives with high yields and enantioselectivities (up to 92% yield, up to 94% ee). Deuterium-labelling experiments indicate that phenylphosphinic acid plays a pivotal role in the DKR of α-keto-β-lactams by promoting the enolization process. The synthetic potential of this protocol was demonstrated by its application in the synthesis of a key intermediate of Taxol and (+)-epi-Cytoxazone. This journal is

Visible light photocatalytic aerobic oxidative synthesis of imines from alcohols and amines on dye-sensitized TiO2

A general visible light photocatalytic protocol for the synthesis of imines via a two-step one-pot route on alizarin red S (ARS)-sensitized TiO2 was uncovered. This efficient synthesis protocol involves one step of the highly selective formation of aldehydes from the oxidation of alcohols with O2 on ARS-sensitized TiO2 photocatalyst, and a subsequent step of condensation of newly formed aldehydes with various amines on TiO2 to afford imines in one pot. Anatase TiO2 provides a versatile platform for catalytic amounts of ARS (0.67 mol%) to facilitate the electron transfer from dye traversing its conduction band to O2 under green LED irradiation. Moreover, the Lewis acid sites of TiO2 can promote the formation of imines from aldehydes and amines in very high isolated yields. We took advantage of both the photocatalytic and catalytic properties of TiO2 to significantly expand the scope of imines. Our work suggests that the synthetic applications of TiO2 photocatalysis can be achievable under mild conditions by exploring the excellent functionalities of TiO2.

Visible-light-induced regioselective cross-dehydrogenative coupling of 2 H-indazoles with ethers

A visible-light-promoted regioselective C(sp2)-H/C(sp3)-H cross-dehydrogenative coupling between 2H-indazoles and ethers has been achieved using a catalytic amount of rose bengal as an organophotoredox-catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant at ambient temperature under aerobic conditions. A variety of C-3 oxyalkylated 2H-indazoles have been synthesized in moderate to good yields. Mechanistic studies suggest a radical pathway of the present reaction.

Ru Nanoparticles-Loaded Covalent Organic Framework for Solvent-Free One-Pot Tandem Reactions in Air

Condensation of benzene-1,3,5-tricarbohydrazide with benzene-1,4-dicarboxaldehyde generated a new covalent organic framework, COF-ASB (1), in which the organic units are held together via hydrazone linkage to form porous frameworks. COF-ASB (1) is highly crystalline and displays good chemical and thermal stability and is permanently porous. In addition, 1 can be an ideal support to load Ru nanoparticles (Ru NPs) to generate Ru@COF-ASB (2). The obtained composite material is able to highly promote one-pot tandem synthesis of imine products from benzyl alcohols and corresponding amines under solvent-free conditions in air.

Paclitaxel Biosynthesis: Adenylation and Thiolation Domains of an NRPS TycA PheAT Module Produce Various Arylisoserine CoA Thioesters

Structure-activity relationship studies show that the phenylisoserinyl moiety of paclitaxel (Taxol) is largely necessary for the effective anticancer activity. Several paclitaxel analogues with a variant isoserinyl side chain have improved pharmaceutical

Recyclable hydrotalcite catalysts for alcohol imination via acceptorless dehydrogenation

Here we report that hydrotalcite-like materials (HTs) are active heterogeneous catalysts for alcohol imination, which proceeds through acceptorless alcohol dehydrogenation. The catalytic activity of a series of Mg-Al hydrotalcites doped with Fe3+, Zn2+, Ni2+, Cr3+ and Cu2+ is dependent on their composition, and Fe : Mg : Al HT yields up to 92% imine under mild conditions. Impregnation of Fe : Mg : Al HT with Pd0 resulted in an enhancement of activity for acceptorless dehydrogenation, but a decrease in the isolated yield of imine in a loading-dependent manner. This is attributed to the Pd loading-dependent retention of imine and aldehyde on the catalysts. The substrate scope for alcohol imination and recyclability of the catalysts is discussed.

Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: A facile access to α-methylene γ-lactams

The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized α-amino nitriles, which could be readily converted into α-methylene-γ-butyrolactams. The Royal Society of Chemistry 2012.