7196-05-6

Upstream product

• 14385-49-0 8-(4'-methoxyphenoxy)acetophenone 
• 53074-73-0 2-(2-chloroacetyl)phenol 
• 100-58-3 phenylmagnesium bromide 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 150-76-5 4-methoxy-phenol 
• 70-11-1 α-bromoacetophenone 
• 62594-98-3 4-methoxy-2-(1-phenylethenyl)phenol 
• 536-74-3 phenylacetylene 

Downstream Products

• 7291-76-1 5-hydroxy-3-phenylbenzofuran 

Relevant academic research and scientific papers

B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with Phenols

We developed a B(C6F5)3 catalyzed hydroarylation of terminal alkynes with various phenols at room temperature without adding any additives, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. Those transformations featured a broad substrate scope with moderate yields. Mechanism studies indicated that those transformations proceeded through the activation of phenol by B(C6F5)3 with subsequent protonation of alkyne/Friedel-Crafts-type reaction. (Figure presented.).

Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent

Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.

Sequential One-Pot Synthesis of 3-Arylbenzofurans from N-Tosylhydrazones and Bromophenol Derivatives

A divergent and efficient one-pot sequence allowing direct access to 3-arylbenzofuran derivatives has been developed. The process, involving N-tosylhydrazones and bromophenols, proceeds via a palladium-catalyzed Barluenga-Valdés cross-coupling, followed by an aerobic, copper-catalyzed, radical cyclization to form Csp2-Csp2 and O-Csp2 bonds. 3-Arylated benzofurans bearing various substituents were obtained with good to excellent yields (up to 90%). Mechanistic investigation strongly supports a radical process for the cyclization step.

Nickel catalyzed intramolecular oxidative coupling: synthesis of 3-aryl benzofurans

Recent research has been focused on the transition metal-catalyzed reactions. Herein we have developed nickel-catalyzed synthesis of 3-aryl benzofurans fromortho-alkenyl phenolsviaintramolecular dehydrogenative coupling. Notably, simple O2gas served as an oxidant, without using any sacrificial hydrogen acceptor. The strategy enabled the synthesis of 3-aryl benzofurans in good to excellent yields.

Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis

Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1)participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5)and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29)as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.

Exogenous-oxidant-free electrochemical oxidative C-H sulfonylation of arenes/heteroarenes with hydrogen evolution

An efficient and environmentally benign electrochemical oxidative radical C-H sulfonylation of arenes/heteroarenes was developed in this work. A series of significant diarylsulfones were prepared under mild catalyst- and exogenous-oxidant-free reaction conditions, which efficiently avoid the issues of desulfonylation or over-reduction of sulfonyl groups.

TfOH-SiO2 as an efficient and recyclable catalyst for synthesis of 3-arylbenzofurans

A convenient process for the synthesis of 3-arylbenzofurans and their derivatives by 2-phenoxy-1-phenylethanones via TfOH-SiO2 catalyzed is developed. This method provides several advantages such as simple work-up procedure, simple post-treatme

Iodine-Mediated, Microwave-Assisted Synthesis of 1-Arylnaphthofurans via Cyclization of 1-(1′-Arylvinyl)-2-naphthols

A metal-free, one-pot, iodine-mediated, microwave-assisted cyclization of 1-(1′-arylvinyl)-2-naphthols (ortho-vinylnaphthols) into 1-arylnaphthofurans is developed. The 1-arylnaphthofurans are isolated in good to excellent yields (65-90%) using two equiva

Controlled synthesis of 2-and 3-substituted benzo[ b ]furans

A controlled regioselective synthesis of either C-2 or C-3 substituted benzo[b]furans from readily accessible 1-(2-hydroxyphenyl)-2-chloroethanones is described. Addition of a range of Grignard reagents to the α-chloro ketones generates alkoxide intermediates, which can form either 2-substituted benzo[b]furans via a [1,2]-aryl migration or 3-substituted benzo[b]furans via a direct cyclization and dehydration sequence. A temperature-dependent [1,2]-aryl migration mechanism for the formation of 2-substituted benzo[b]furan is proposed.

Natural tanshinone-like heterocyclic-fused ortho-quinones from regioselective Diels-Alder reaction: Synthesis and cytotoxicity evaluation

A series of new natural tanshinone-like oxoheterocyclic-fused ortho-quinone derivatives were synthesized from readily available benzofuranol and N-substituted dienes via IBX oxidation-cycloaddition-aromatization procedure. The regiospecific Diels-Alder cycloaddition reactions of N-dienes were achieved efficiently with a variety of dienophiles. It is found that the amide moiety in the molecular could be preserved or eliminated by control of the aromatization conditions. Selected oxoheterocyclic-fused ortho-quinones as well as several thioheterocyclic-fused ortho-quinones we obtained before were evaluated for their cytotoxicities on different cancer cell lines and the Structure-Activity Relationship (SAR) was discussed.