21847-98-3

Upstream product

• 38136-29-7 4-methylvaleroyl chloride 
• 108-88-3 toluene 
• 1757-42-2 3-methyl-cyclopentanone 
• 4463-41-6 2-(p-tolyl)-1,3,2-dioxaborinane 
• 513-38-2 Isobutyl iodide 
• 766-97-2 4-n-methylphenylacetylene 
• 73177-66-9 4-methyl-1-(4-methylphenyl)-1-pentanol 
• 104-87-0 4-methyl-benzaldehyde 
• 4548-78-1 (3-methylbutyl)magnesium bromide 
• 874-60-2 4-methyl-benzoyl chloride 
• 104-85-8 para-methylbenzonitrile 
• 22422-21-5 4'-methyl-3-chloropropiophenone 
• 1539-32-8 4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 

Downstream Products

• 104455-10-9 2-Bromo-4-methyl-1-(4-methylphenyl)pentan-1-one 

Relevant academic research and scientific papers

Preparation method of diabetes-treating medicine, namely ipragliflozin or derivative thereof

The invention provides a preparation method of a diabetes-treating medicine, namely ipragliflozin or a derivative thereof. According to the preparation method, alpha-O-alkenyl sulfone is used as an electrophilic reagent for the Suzuki-Miyaura coupling reaction; the reaction raw material alpha-O-alkenyl sulfone is simple to prepare and stable in structure, and can overcome the defects of instability, preparation difficulty and the like when organic halide and sulfonic acid are used as electrophilic reagents for the Suzuki-Miyaura coupling reaction. Meanwhile, the reaction are mild in reaction conditions, compatible with a wide range of heterocyclic rings and various functional groups, high in yield and capable of realizing large-scale process production. Since alpha-O-alkenyl sulfone is used as the electrophilic reagent for the Suzuki-Miyaura coupling reaction, high-yield generation of aryl glucoside and open-chain alkenyl ether can be realized, medicines for treating type 2 diabetes mellitus, namely ipragliflozin and 2-deoxyipragliflozin can also be prepared, and the application scope of the preparation method is wide.

Suzuki-Miyaura coupling reaction using alpha-O-alkenyl sulfone as electrophilic reagent and application thereof

The invention provides a Suzuki-Miyaura coupling reaction using alpha-O-alkenyl sulfone as an electrophilic reagent. The reaction comprises the following steps: weighing alpha-O-alkenyl sulfone, an organic boron reagent, a ligand, an alkali and a catalyst, and carrying out reacting in a solvent. The invention also provides application of the coupling reaction. According to the invention, alpha-O-alkenyl sulfone is used as the electrophilic reagent for the Suzuki-Miyaura coupling reaction, and the reaction raw material alpha-O-alkenyl sulfone is simple to prepare and stable in structure, and can overcome the defects of instability, preparation difficulty and the like when organic halide and sulfonic acid are used as electrophilic reagents for the Suzuki-Miyaura coupling reaction. Meanwhile,the reaction are mild in reaction conditions, compatible with a wide range of heterocyclic rings and various functional groups, high in yield and capable of realizing large-scale process production.Since the alpha-O-alkenyl sulfone is used as the electrophilic reagent for the Suzuki-Miyaura coupling reaction, high-yield generation of aryl glucoside and open-chain alkenyl ether can be realized, medicines for treating type 2 diabetes mellitus, namely ipragliflozin and 2-deoxyipragliflozin can also be prepared, and the application scope of the reaction is wide.

Mn-Enabled Radical-Based Alkyl-Alkyl Cross-Coupling Reaction from 4-Alkyl-1,4-dihydropyridines

Highly efficient alkylation of β-chloro ketones and their derivatives was achieved by means of domino dehydrochlorination/Mn-enabled radical-based alkyl-alkyl cross-coupling reaction. In situ-generated α,β-unsaturated ketones and their analogues were identified as the reaction intermediates. Known bioactive compounds, such as melperone and azaperone, could be easily prepared from β-chloropropiophenone in two steps.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Iron-Catalyzed Synthesis of Dihydronaphthalenones from Aromatic Oxime Esters

Herein, a convenient procedure on iron-catalyzed radical-mediated synthesis of dihydronaphthalenones from oxime esters has been developed. By using iron salt as a green and inexpensive catalyst, various α-aryl oxime esters were transformed into the corresponding dihydronaphthalenones in moderate to good yields with high chemo-selectivities. The reaction proceeds via 1,5-hydrogen atom transfer and then intramolecular radical cyclization sequence. (Figure presented.).

Carbonylation of tertiary carbon radicals: synthesis of lactams

Herein, we disclose an interesting iron-catalyzed approach for the carbonylation of a tertiary carbon radical. The tertiary carbon radical generated from a 1,5-hydrogen atom transfer can be captured by CO gas smoothly. Various six-membered lactams were constructed chemo-selectively in high yields.

Regioselective Vinylation of Remote Unactivated C(sp3)?H Bonds: Access to Complex Fluoroalkylated Alkenes

Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C?H bonds is of great synthetic value. Despite advances in radical-mediated functionalization of C(sp3)?H bonds by a hydrogen-atom transfer process, the site-selective vinylation of remote C(sp3)?H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp3)?H bonds. The remote C(sp3)?H activation is promoted by a C-centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri-/di-/mono-fluoromethyl and perfluoroalkyl groups.

Iron-Catalyzed Oxyalkylation of Terminal Alkynes with Alkyl Iodides

A general oxyalkylation of terminal alkynes enabled by iron catalysis has been developed. Primary and secondary alkyl iodides acted as the alkylating reagents and afforded a range of α-alkylated ketones under mild reaction conditions. Acetyl tert-butyl peroxide (TBPA) was used as the radical relay precursor, providing the initiated methyl radical to start the radical relay process. Preliminary mechanistic studies were conducted, and late-stage functionalizations of natural product derivatives were performed.

Suzuki-Miyaura coupling of simple ketones via activation of unstrained carbon-carbon bonds

Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic ketones. Preliminary mechanistic study suggests that the ketone α-C-C bond was cleaved via oxidative addition.