5782-17-2Relevant academic research and scientific papers
Iridium-Catalyzed Aerobic Coupling of Salicylaldehydes with Alkynes: A Remarkable Switch of Oxacyclic Product
Yamane, Shintaro,Hinoue, Tomoaki,Usuki, Yoshinosuke,Itazaki, Masumi,Nakazawa, Hiroshi,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro,Satoh, Tetsuya
supporting information, p. 7852 - 7855 (2018/05/08)
The iridium(III)/copper(II)-catalyzed dehydrogenative coupling of salicylaldehydes with internal alkynes proceeds efficiently under atmospheric oxygen through aldehyde C?H bond cleavage and decarbonylation. A variety of benzofuran derivatives can be synthesized by the environmentally benign procedure. DFT calculations suggest that this unique transformation involves the facile deinsertion of CO in the key metallacycle intermediate, which is in marked contrast to the corresponding rhodium(III) catalysis that leads to CO-retentive chromone derivatives.
Natural product inspired library synthesis - Identification of 2,3-diarylbenzofuran and 2,3-dihydrobenzofuran based inhibitors of Chlamydia trachomatis
Saleeb, Michael,Mojica, Sergio,Eriksson, Anna U.,Andersson, C. David,Gylfe, ?sa,Elofsson, Mikael
supporting information, p. 1077 - 1089 (2017/12/15)
A natural product inspired library was synthesized based on 2,3-diarylbenzofuran and 2,3-diaryl-2,3-dihydrobenzofuran scaffolds. The library of forty-eight compounds was prepared by utilizing Pd-catalyzed one-pot multicomponent reactions and ruthenium-catalyzed intramolecular carbenoid C-H insertions. The compounds were evaluated for antibacterial activity in a panel of test systems including phenotypic, biochemical and image-based screening assays. We identified several potent inhibitors that block intracellular replication of pathogenic Chlamydia trachomatis with IC50 ≤ 3 μM. These new C. trachomatis inhibitors can serve as starting points for the development of specific treatments that reduces the global burden of C. trachomatis infections.
Photoinduced Gold-Catalyzed Domino C(sp) Arylation/Oxyarylation of TMS-Terminated Alkynols with Arenediazonium Salts
Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Lázaro-Milla, Carlos
, p. 2177 - 2186 (2017/02/26)
A selective and convenient synthesis of tri- and tetrasubstituted α,β-unsaturated ketones, as well as 2,3-diarylbenzofurans has been developed with the aid of light and taking advantage of a cooperative gold/photoredox-catalyzed 2-fold arylation reaction of TMS-terminated alkynols. The reaction of 3-(trimethylsilyl)prop-2-yn-1-ols was competent to generate diarylated α,β-unsaturated ketones; whereas the photoredox sequence involving 2-[(trimethylsilyl)ethynyl]phenol exclusively afforded 2,3-diarylbenzofurans. The reaction of terminal alkynes proceeded in poor yields while the use of bulkier silyl groups, such as TIPS, resulted unproductive. Apparently, the C(sp) arylation reaction is the first event on the domino bis-arylative sequence. These results could be explained through the intermediation of arylgold(III) species and several single electron transfer processes.
Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis
Rao, Maddali L. N.,Talode, Jalindar B.,Murty, Venneti N.
supporting information, p. 2065 - 2076 (2016/10/05)
A regio- and chemoselective cross-coupling study using 2,3-dibromobenzofurans and 2,3,5-tribromobenzofuran was achieved with sub-stoichiometric loadings of triarylbismuths as atom-economic reagents under Pd-catalyzed conditions. As part of this study, various 2,3-diaryl- and 2,3,5-triarylbenzofuran products were obtained in high yields, involving one-pot operations and short reaction times.
Synthesis of arylated benzofurans by regioselective Suzuki-Miyaura cross-coupling reactions of 2,3-dibromobenzofurans- and 2,3,5-tribromobenzofurans
Hussain,Thai Hung,Abbas,Khera,Malik,Patonay,Kelzhanova,Abilov,Villinger,Langer
, p. 497 - 505 (2015/03/30)
Arylated benzofurans were prepared by regioselective Suzuki-Miyaura cross-coupling reactions of 2,3-dibromobenzofuran. The reactions proceeded with very good site-selectivity in favor of the more electron deficient position 2. The Suzuki-Miyaura reactions
A one-pot domino C-H, C-C activation in coumarins: A fast track to 2,3-diaryl benzo[b]furans
Khoobi, Mehdi,Molaverdi, Fatemeh,Jafarpour, Farnaz,Abbasnia, Masoumeh,Kubicki, Maciej,Shafiee, Abbas
supporting information, p. 11713 - 11716 (2015/07/15)
An approach to synthesize 2,3-diaryl benzo[b]furans using coumarins and aryl bromides is developed. This state-of-the-art strategy capitalizes on a palladium-catalyzed one-pot decarbonylative diarylation of coumarins, paving the way to achieve biologicall
Palladium-catalyzed synthesis of benzofurans via C-H activation/oxidation tandem reaction and its application to the synthesis of decursivine and serotobenine
Guo, Lei,Zhang, Fengying,Hu, Weimin,Li, Lei,Jia, Yanxing
, p. 3299 - 3302 (2014/03/21)
A new palladium-catalyzed method for the synthesis of benzofurans by reaction of 2-hydroxystyrenes and iodobenzenes via a C-H activation/oxidation tandem reaction has been unprecedentedly discovered. By using this strategy, the overall synthetic efficienc
Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity
Liu, Guixia,Shen, Yangyang,Zhou, Zhi,Lu, Xiyan
, p. 6033 - 6037 (2013/07/19)
Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)-catalyzed C-H functionalization of N-phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho-hydroxyphenyl-substituted enamides or cyclization to deliver benzofurans with high selectivity (see scheme; Cp=C5Me5). Copyright
