Abstract
Pd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-DCE, using 5 mol% Pd (OAc)2 and 2 eq. of CuCl2 at 80 °C, produced a variety of 2-arylbenzofurans in moderate-to-high yields. The reaction is sensitive to the electronic nature of the substituents on the benzene ring of the triarylantimony difluorides: an electron-donating group showed higher reactivity than an electron-withdrawing group. Single crystal X-ray analysis of tri(p-methylphenyl) antimony difluoride revealed that the central antimony atom exhibits trigonal bipyramidal geometry.
Highlights
Academic Editor: Haibo Ge tri(p-methylphenyl) antimony difluoride revealed that the central antimony atom exhibits trigonal bdLioip2nCyiOuram3 m[2tie4dt,r2aa5lf]lg.ueGoorloombrieoutrsrayte.et al revealed that progresses using
McGlacken and Wan independently reported the use of PdO-Fe3O4 and a solid-based KPdeycwataolrydsst :foCr–tHhearreyalcattioionno;fpbaelnlazdoifurmancantadlydsita;raynliotidmonoinuym; tsraialtrsy[l2a7n,2t8im]. oTnanygdeiflt ualo. ride; benzofuran demonstrated the C–2 arylation of benzofurans using N’-acyl arylhydrazines in the presence of a PdCl2(MeCN)2 catalyst and the 2,2,6,6-tetramethylpiperidine 1-oxyl radical (TEMPO) [29]
Inspired by the aforementioned reports and a continuation of our studies on the C–H arylation of aromatic heterocycles, this paper presents the Pd-catalyzed regioselective arylation of bFeignuzroefu1.rBanioslowgiictahllAy ra3cStibvFe22-faorrytlbheenszyonfuthraensidseorifv2a-taivreysl.benzofurans
Summary
Academic Editor: Haibo Ge tri(p-methylphenyl) antimony difluoride revealed that the central antimony atom exhibits trigonal bdLioip2nCyiOuram m[2tie4dt,r2aa5lf]lg.ueGoorloombrieoutrsrayte.et al revealed that progresses using. Ride; benzofuran demonstrated the C–2 arylation of benzofurans using N’-acyl arylhydrazines in the presence of a PdCl2(MeCN) catalyst and the 2,2,6,6-tetramethylpiperidine 1-oxyl radical (TEMPO) [29]. These procedures could be used complementarily; each reaction has several drawbacks in substrate scope and efficiency. McGlacken and Wan independently reported the use of PdO-Fe3O4 and a solid-based Pd catalyst for the reaction of benzofuran and diaryliodonium salts [27,28]. Demonstrated the C–2 arylation of benzofurans using N’-acyl arylhydrazines in the presence of a PdCl2(MeCN) catalyst and the 2,2,6,6-tetramethylpiperidine 1-oxyl radical (TEMMPaOn)y[2m9]e.tThhodessehparvoecebdeuernesdceovuelldopbedusfoedr tchoemspylnemtheensitsaroilfy2; -haorwylebveenrz,oefaucrharnesa.ctPiodnchaatsalsyezveedradlidrercatwCb–aHckasriynlastuiobnstoraft5e-msceompebearnedd ehfefitceireonacryo.mTahteicrecfomrep, tohuendesviselonpemoefntthoef manosetffpeoctwiveerfnuolvtoeol lasryfolrdtohneosryannthdetshise oefluacriydlatieodnhoefteitrsorceyaccletisv[it1y3,f1o4r].th2e-ACr–yHlbeanryzloaftuiorannosf hbaevnezobfeuernanprdeepraivraetdiviens tahries wreaqyuiuresdin. Doucet et al reported the reaction of benzofurans and aryl sulfonyl chlorides in the presence of
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