20851-07-4

Upstream product

• 13249-75-7 (Z)-1,2,4-triphenyl-2-butene-1,4-dione 
• 4441-01-4 1,2,4-triphenylbutane-1,4-dione 
• 108-86-1 bromobenzene 
• 136340-87-9 N-(2-thenoyl)-2-methylaniline 
• 31599-59-4 2-(diacetoxyiodo)toluene 
• 615-37-2 ortho-methylphenyl iodide 
• 4363-35-3 Dihydroxy-styryl-boran 
• 3328-86-7 2,4-diphenylthiophene 
• 66003-76-7 Diphenyliodonium triflate 
• 591-50-4 iodobenzene 
• 16939-12-1 2,3-diphenylthiophene 
• 1240039-08-0 C₂₂H₁₆I₂ 
• 88-13-1 3-Thiophene carboxylic acid 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Complexes of palladium(II) with N-heterocyclic carbenes from adamantylimidazole as precatalysts for thiophene and imidazole arylation

Complexes of palladium(II) with N-heterocyclic carbenes of the PEPPSI-type were synthesized by the reaction of PdCl2 with 1-adamantyl-3-(R-methyl)-1H-imidazolium salts. These complexes were used as productive precatalysts for substituted thioph

Cu-catalyzed [2 + 2 + 1] cascade annulation of vinyl iodonium salts with elemental sulfur/selenium for the modular synthesis of thiophenes and selenophenes

A [2 + 2 + 1] annulation protocol has been established for the modular synthesis of 2,4-disubstituted thiophenes/selenophenes, with excellent regioselectivity. The reactions have been catalyzed by copper salt with elemental sulfur and selenium serving as

Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles

An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.

Access to Substituted Thiophenes through Xanthate-Mediated Vinyl C(sp2)-Br Bond Cleavage and Heterocyclization of Bromoenynes

An environmentally sustainable strategy for the chemoselective heterocyclization of bromoenynes through a transition-metal-free sulfuration/cyclization process is reported. Using inexpensive and safe EtOCS2K as a thiol surrogate and tetrabutylphosphonium bromide and H2O as a mixed solvent, the reaction provided a range of substituted thiophenes in moderate to good yields. In addition, 2,3,4,5-tetrasubstituted thiophenes were able to be prepared under mild reaction conditions by electrophilic heterocyclization with NH4I and EtOCS2K in good yields.

A trisulfur radical anion (S3-) involved sulfur insertion reaction of 1,3-enynes: Sulfide sources control chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides

Cascade cyclization reactions of S3-in situ generated from S2- with 1,3-enynes for the chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides controlled by sulfide salts are develop

Adamantanyl-substituted PEPPSI-type palladium(II) N-heterocyclic carbene complexes: synthesis and catalytic application for CH activation of substituted thiophenes

[Figure not available: see fulltext.] Starting from 1-adamantanyl-3-imidazole, a number of new 1-adamantanyl-3-benzylimidazolium salts and corresponding unsymmetrically substituted Pd(II) PEPPSI-type complexes were prepared, including dichloride, dibromide, and diiodide. Single crystal X-ray crystallography confirmed solid state structures in six cases. The complexes reported in this work displayed moderate activities as precatalysts for CH activation/arylation reaction of substituted thiophenes.

Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds

A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.

In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is

Cu-catalyzed double S-alkenylation of potassium sulfide: A highly efficient method for the synthesis of various thiophenes

An efficient synthetic approach to variously substituted thiophenes has been developed through copper-catalyzed tandem S-alkenylation of potassium sulfide with 1,4-diiodo-1,3-dienes.