98437-24-2

Usage

Uses

Used in Organic Synthesis:
Benzofuran-2-boronic acid is used as a reagent for the facile preparation of highly-functionalized, nitrogen-bearing diarylmethanes. This application is valuable for the synthesis of complex organic molecules and compounds with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H7BO3/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-5,10-11H

Upstream product

• 1104637-65-1 2-benzofuranylboronic acid mida ester 
• 7732-18-5 water 
• 271-89-6 1-benzofurane 
• 121-43-7 Trimethyl borate 
• 701-99-5 Phenoxyacetyl chloride 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 122-59-8 2-phenoxyacetic acid 
• 108-95-2 phenol 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 36078-99-6 2-(4-(methoxycarbonyl)phenyl)benzo[b]furan 
• 53348-90-6 4-(benzofuran-2-yl)benzaldehyde 
• 121668-46-0 2-(benzofuran-2-yl)benzoic acid 
• 36078-98-5 4-(Benzofuran-2-yl)benzoic acid 
• 797790-41-1 3-benzofuran-2-yl-benzo[1,4]oxazine-4-carboxylic acid phenyl ester 
• 680971-69-1 3-benzofuran-2-yl-pyrido[3,2-b][1,4]oxazine-4-carboxylic acid phenyl ester 

Relevant academic research and scientific papers

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes

The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[b]heteroole 15. Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.

Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors

Based on perlolyrine (1), a natural alkaloid with weak PDE5 potency from the traditional Chinese aphrodisiac plant Tribulus terrestris L., a series α-substituted tetrahydro-β-carboline (THβC) derivatives were synthesized via T+BF4--mediated oxidative C–H functionalization of N-aryl THβCs with diverse potassium trifluoroborates. Following Winterfeldt oxidation afforded the corresponding furyl/thienyl pyrroloquinolones, of which 5-ethylthiophene/ethylfuran derivatives 20a–b were identified as the most potent and selective PDE5 inhibitors. Among the enantiomers, (S)-20a and (S)-20b (IC50 = 0.52 and 0.39 nM) were found to be more effective than their (R)-antipode, display favorable pharmacokinetic profiles, exert in vitro vasorelaxant effects on the isolated thoracic aorta, and exhibit in vivo efficacy in the anesthetized rabbit erectile model.

Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus

In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential.

SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.