17293-66-2

Upstream product

• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 46188-84-5 1‐(4‐methoxyphenyl)‐2‐(methylsulfanyl)ethanone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 768-60-5 4-methoxyphenylacetylen 
• 74-88-4 methyl iodide 
• 624-92-0 Dimethyldisulphide 
• 4973-66-4 methyl thiotosylate 

Relevant academic research and scientific papers

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

Copper-catalyzed thiolation of terminal aromatic alkynes to access alkynyl disulfides

A copper-catalyzed thiolation of terminal aromatic alkynes by disulfur transfer to access alkynyl disulfides was developed. Different types of products were afforded due to the steric hindrance of dithiolsulfonates. Some important compounds, such as fully substituted triazoles and pyrene-gemcitabine conjugate were prepared by this new approach.

Synthesis of Alkynyl Sulfides by Copper-Catalyzed Thiolation of Terminal Alkynes Using Thiosulfonates

A mild and odorless copper-catalyzed thiolation of terminal alkynes with thiosulfonates is described. The broad substrate scope provides convenient access to a wide variety of sulfur-containing heterocycles. In particular, divergent benzoheteroles are efficiently prepared in a simple manner by thiolation of ethynylbenzenes bearing ortho-nucleophilic functional groups followed by iodocyclization.

Accessing the Rare Diazacyclobutene Motif

A formal [2 + 2] cycloaddition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with electron-rich alkynyl sulfides and selenides is described. These investigations provide a convenient method to access diazacyclobutenes in good yield while tolerating a rela

A Highly Regio- and Stereoselective Syntheses of α-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems

A metal-free regio- and stereoselective method is achieved for the preparation of (E)-configured α-halo enamides, vinyl thioethers, and vinyl ethers using aqueous HX (X = F, Cl, Br, I), which features high functional group compatibility and regio- and stereoselectivity, mild conditions, high efficiency, and rapid transformation. Additionally, the isomers could be yielded readily from the (E)-configured α-halo enamides via photocatalysis or under Sonogashira coupling conditions.

Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles

Non-oxidative, regioselective, and convergent access to densely functionalized oxazoles is realized in a functional-group tolerant manner using alkynyl thioethers. Sulfur-terminated alkynes provide access to reactivity previously requiring strong donor-substituted alkynes such as ynamides. Sulfur does not act in an analogous donor fashion in this gold-catalyzed reaction, thus leading to complementary regioselective outcomes and addressing the limitations of using ynamides.

One-pot preparation of arylethynyl sulfides and bis(arylethynyl) sulfides

An efficient preparation for arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished through a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, without the use of various terminal arylacetylenes as substrates. When lithium hexamethyldisilazane (LHMDS), ClP(O)(OEt)2, and LHMDS were sequentially added to a tetrahydrofuran solution of different substrates [arylethanonyl sulfides or bis(arylethanonyl) sulfides], 1 or 2 were obtained in moderate to good yields. The reaction procedure involves the formation of an enol phosphate and a subsequent base-induced elimination. An efficient preparation of arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished by a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, to give 1 and 2 in moderate to good yields. The reaction mechanism involves the formation of an enol phosphate that undergoes a subsequent base-induced elimination. Copyright