259739-70-3

Upstream product

• 80778-47-8 1-iodo-2-methoxymethoxybenzene 
• 533-58-4 2-Iodophenol 
• 1620889-11-3 1-(methoxymethoxy)-2-(p-tolylethynyl)benzene 
• 629-05-0 n-octyne 
• 766-97-2 4-n-methylphenylacetylene 
• 32865-61-5 2-iodophenyl acetate 

Downstream Products

• 58491-52-4 2-(4-methylphenyl)benzofuran-3-carboxylic acid 
• 25664-48-6 2-p-tolyl-benzofuran 
• 1123630-30-7 (E)-3-styryl-2-(p-tolyl) benzofuran 
• 1123630-37-4 (Z)-3-(2-p-tolylbenzofuran-3-yl)but-2-enenitrile 
• 1123630-26-1 (E)-3-(2-p-tolylbenzofuran-3-yl)but-2-enenitrile 
• 1123630-15-8 3-(2-p-tolylbenzofuran-3-yl)cyclohex-2-enone 
• 1123630-17-0 3-(2-p-tolylbenzofuran-3-yl)cyclopent-2-enone 
• 1123630-21-6 (E)-3-(2-p-tolylbenzofuran-3-yl)but-2-enamide 
• 1123630-34-1 3-(2-p-tolylbenzofuran-3-yl)but-3-enamide 
• 1123630-08-9 (E)-methyl 3-(2-p-tolylbenzofuran-3-yl)but-2-enoate 
• 1123630-32-9 methyl 3-(2-p-tolylbenzofuran-3-yl)but-3-enoate 
• 1123629-93-5 butyl (E)-3-(2-p-tolylbenzofuran-3-yl)propenoate 
• 1123630-10-3 (E)-4-(2-p-tolylbenzofuran-3-yl)but-3-en-2-one 
• 1123630-12-5 (E)-4-(2-p-tolylbenzofuran-3-yl)pent-3-en-2-one 

Relevant academic research and scientific papers

Metal-Free Radical Annulation of Oxygen-Containing 1,7-Enynes: Configuration-Selective Synthesis of (E)-3-((Arylsulfonyl)methyl)-4-Substituted Arylidenechromene Derivatives

A novel strategy for the synthesis of (E)-3-((arylsulfonyl)methyl)-4-substituted benzylidenechromene derivatives via a metal-free radical annulation reaction of oxygen-containing 1,7-enynes with thiosulfonates has been developed. The reaction shows broad substrate scope, wide functional group tolerance, and moderate to excellent yields. Moreover, thiosulfonates were well driven to achieve the bifunctionalization reaction of oxo-1,7-enynes which derived from aliphatic alkynes. In addition, the (E)-configuration of the products was highly controlled by the structure of 1,7-enyne.

A Facile Construction of Bisheterocyclic Methane Scaffolds through Palladium-Catalyzed Domino Cyclization

A convenient palladium-catalyzed domino cyclization reaction for the construction of bis(benzofuranyl)methane scaffolds bearing an all-carbon quaternary center has been described. In the cascade process, one C(sp2)—O bond, two C(sp2)—C(sp3) bonds as well as two benzofuran rings are formed in a single synthetic sequence. The approach shows wide scope of substrates and good functional-group tolerance. Moreover, this methodology is successfully extended to the synthesis of benzofuranyl methyl chromane derivatives.

Light-Induced Mechanistic Divergence in Gold(I) Catalysis: Revisiting the Reactivity of Diazonium Salts

In a systematic study of the Au-catalyzed reaction of o-alkynylphenols with aryldiazonium salts, we find that essentially the same reaction conditions lead to a change in mechanism when a light source is applied. If the reaction is carried out at room temperature using a AuI catalyst, the diazonium salt undergoes electrophilic deauration of a vinyl AuI intermediate and provides access to substituted azobenzofurans. If the reaction mixture is irradiated with blue LED light, C?C bond formation due to N2-extrusion from the diazonium salt is realized selectively, using the same starting materials without the need for an additional photo(redox) catalyst under aerobic conditions. We report a series of experiments demonstrating that the same vinyl AuI intermediate is capable of producing the observed products under photolytic and thermal conditions. The finding that a vinyl AuI complex can directly, without the need for an additional photo(redox) catalyst, result in C?C bond formation under photolytic conditions is contrary to the proposed mechanistic pathways suggested in the literature till date and highlights that the role of oxidation state changes in photoredox catalysis involving Au is thus far only poorly understood and may hold surprises for the future. Computational results indicate that photochemical activation can occur directly from a donor–acceptor complex formed between the vinyl AuI intermediate and the diazonium salt.

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole-Transport Properties

Thienoacenes and furoacenes are among the most frequent molecular units found in organic materials. The efficient synthesis of morphologically different heteroacenes and the rapid determination of their solid-state and electronic properties are still challenging tasks, which slow down progress in the development of new materials. Here, we report a flexible and efficient synthesis of unprecedented heterotetracenes based on a platinum- and gold-catalyzed cyclization–alkynylation domino process using EthynylBenziodoXole (EBX) hypervalent iodine reagents in the key step. The proof-of-principle in silico estimation of the synthesized tetracenes’ charge transport properties reveals their strong dependence on both the position and nature of the heteroatoms in the ring system. A broad range of mobility is predicted, with some compounds displaying performance potentially comparable to that of state-of-the-art electronic organic materials.

Copper-Iodide- and Diorganyl-Diselenide-Promoted Cyclization of 2-Alkynylphenols: Alternative Approach to 3-Organoselanylbenzo[b]furans

This paper describes an alternative method for the synthesis of 3-organoselanylbenzo[b]furans through the intramolecular cyclization of 2-alkynylphenols promoted by copper iodide and diorganyl diselenides. The cyclization reactions were carried out at roo

A Palladium-Catalyzed Domino Approach to 2,3-Disubstituted Benzofurans via an Intermolecular Carbopalladation/C(sp3)?H Functionalization/Isomerization Sequence

A palladium-catalyzed domino strategy has been developed for the synthesis of 2,3-disubstituted benzofuran derivatives. This cascade reaction sequence involves intermolecular carbopalladation and C(sp3)?H functionalization followed by isomerization. (Figure presented.).

Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans

A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient app

A concise approach for the synthesis of 3-iodoindoles and 3-iodobenzo[b]furans via Ph3P-catalyzed iodocyclization

A variety of 3-iodoindole and 3-iodobenzo[b]furan derivatives were conveniently prepared from the corresponding 2-alkynylanilines and 2-alkynylphenols through Ph3P-catalyzed iodocyclization in the presence of N-iodosuccinimide (NIS). This proto

Highly efficient heterogeneous synthesis of benzofurans under aqueous condition

Highly efficient organic reactions in water are important for designing environmental-friendly and low cost synthetic processes. Herein, we demonstrate an intermediate-in-water strategy for the heterogeneous synthesis of benzofurans in aqueous media. The cyclization reaction of 2-(phenylethynyl)phenol to 2-phenylbenzofuran cannot proceed in pure water. However, this reaction can be efficiently promoted by the formation of sparingly soluble intermediate in the presence of alkaline. Quantitative conversion of a variety of substrates to benzofuran derivatives has been achieved in the absence of noble metal catalyst. Other remarkable features including easy-isolation and purification of product, along with wide range of functional group tolerance render the methodology promising in the realm of green-synthesis.

Tandem gold-catalyzed hydrosilyloxylation-aldol and -Mannich reaction with alkynylaryloxysilanols in 6-exo mode

The tandem gold-catalyzed hydrosilyloxylation-aldol and hydrosilyloxylation-Mannich reactions were developed through the formation of an enol silyl ether catalytically generated in situ from alkynylaryloxysilanols in the 6-exo mode in one reaction vessel. Copyright