Palladium‐Catalyzed Regioselective C‐2 Arylation of Benzofurans with N′‐Acyl Arylhydrazines

An efficient and ligand‐free palladium‐catalyzed arylation of benzofurans has been developed with N′ ‐acyl arylhydrazines as the coupling partners. This protocol features a wide functional‐group tolerance and highly regioselective products.

[1]  C. Tai,et al.  Synthesis of Benzofurans and Indoles from Terminal Alkynes and Iodoaromatics Catalyzed by Recyclable Palladium Nanoparticles Immobilized on Siliceous Mesocellular Foam. , 2017, Chemistry.

[2]  Lisa K. Woolhiser,et al.  Development of a Novel Lead that Targets M. tuberculosis Polyketide Synthase 13 , 2017, Cell.

[3]  Rajeshwari,et al.  A review on antioxidant potential of bioactive heterocycle benzofuran: Natural and synthetic derivatives , 2017, Pharmacological reports : PR.

[4]  Zhang Jiquan,et al.  Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines , 2017 .

[5]  V. Hessel,et al.  Mild and selective base-free C–H arylation of heteroarenes: experiment and computation , 2016, Chemical science.

[6]  Le Guo,et al.  A Pincer Ruthenium Complex for Regioselective C-H Silylation of Heteroarenes. , 2016, Organic letters.

[7]  Renhua Liu,et al.  One‐Step Synthesis of Substituted Benzofurans from ortho‐ Alkenylphenols via Palladium‐Catalyzed CH Functionalization , 2016 .

[8]  M. Bosiak.  A Convenient Synthesis of 2-Arylbenzo[b]furans from Aryl Halides and 2-Halophenols by Catalytic One-Pot Cascade Method , 2016 .

[9]  D. J. Ramón,et al.  Impregnated palladium on magnetite as catalyst for direct arylation of heterocycles , 2016 .

[10]  Shamsuzzaman,et al.  Bioactive Benzofuran derivatives: A review. , 2015, European journal of medicinal chemistry.

[11]  Anamik Shah,et al.  Bioactive benzofuran derivatives: An insight on lead developments, radioligands and advances of the last decade. , 2015, European journal of medicinal chemistry.

[12]  A. Chan,et al.  Copper(ii)-catalyzed coupling reaction: an efficient and regioselective approach to N',N'-diaryl acylhydrazines. , 2015, Organic & biomolecular chemistry.

[13]  Kyeong Lee,et al.  Bioactive benzofuran derivatives: moracins A-Z in medicinal chemistry. , 2015, European journal of medicinal chemistry.

[14]  Quan Zhou,et al.  N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed Direct C-H Bond Arylation of Benzo[b]furans with Aryl Chlorides. , 2014, The Journal of organic chemistry.

[15]  E. Raymond,et al.  Benzofuran derivatives as anticancer inhibitors of mTOR signaling. , 2014, European journal of medicinal chemistry.

[16]  Wei Liu,et al.  Direct arylation of pyridines without the use of a transition metal catalyst. , 2014, Chemical communications.

[17]  H. Doucet,et al.  Regiocontroled Palladium‐Catalysed Direct Arylation at Carbon C2 of Benzofurans using Benzenesulfonyl Chlorides as the Coupling Partners , 2014 .

[18]  E. Raymond,et al.  Benzofuran derivatives as a novel class of inhibitors of mTOR signaling. , 2014, European journal of medicinal chemistry.

[19]  K. Akamanchi,et al.  Aryl-free radical-mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application toward the synthesis of benzocarbazoledione. , 2014, The Journal of organic chemistry.

[20]  F. Glorius,et al.  Pd/C als Katalysator für die vollständig regioselektive und milde C-H-Funktionalisierung von Thiophenen† , 2014 .

[21]  F. Glorius,et al.  Pd/C as a catalyst for completely regioselective C-H functionalization of thiophenes under mild conditions. , 2014, Angewandte Chemie.

[22]  N. Jiao,et al.  Catalyst-controlled highly selective coupling and oxygenation of olefins: a direct approach to alcohols, ketones, and diketones. , 2013, Angewandte Chemie.

[23]  Xue‐Wei Liu,et al.  Oxidative Heck reaction of glycals and aryl hydrazines: a palladium-catalyzed C-glycosylation. , 2013, The Journal of organic chemistry.

[24]  Kangning Li,et al.  Palladium‐Catalyzed Direct Denitrogenative C‐3‐Arylation of 1H‐Indoles with Arylhydrazines using Air as the Oxidant , 2013 .

[25]  F. Glorius,et al.  Rhodium(III) und Hexabrombenzol – ein Katalysatorsystem zur gekreuzten dehydrierenden Kupplung einfacher Arene und Heterocyclen mit Arenen mit dirigierenden Gruppen , 2012 .

[26]  F. Glorius,et al.  Rhodium(III) and hexabromobenzene-a catalyst system for the cross-dehydrogenative coupling of simple arenes and heterocycles with arenes bearing directing groups. , 2012, Angewandte Chemie.

[27]  T. Loh,et al.  Palladium-catalyzed C-C bond formation of arylhydrazines with olefins via carbon-nitrogen bond cleavage. , 2011, Organic letters.

[28]  Lei Wang,et al.  Sequential and one-pot reactions of phenols with bromoalkynes for the synthesis of (Z)-2-bromovinyl phenyl ethers and benzo[b]furans. , 2011, Organic letters.

[29]  T. Taniguchi,et al.  A mild oxidative aryl radical addition into alkenes by aerobic oxidation of arylhydrazines. , 2011, Chemistry.

[30]  T. Truong,et al.  Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates. , 2011, Journal of the American Chemical Society.

[31]  H. Saji,et al.  A novel 18F-labeled pyridyl benzofuran derivative for imaging of β-amyloid plaques in Alzheimer's brains. , 2010, Bioorganic & medicinal chemistry letters.

[32]  S. K. Guchhait,et al.  Direct C-H Bond Arylationof (Hetero)arenes with Aryl and Heteroarylboronic Acids , 2010 .

[33]  J. Mata,et al.  Domino Approach to Benzofurans by the Sequential Sonogashira/Hydroalkoxylation Couplings Catalyzed by New N-Heterocyclic-Carbene-Palladium Complexes , 2009 .

[34]  O. Daugulis,et al.  A general method for copper-catalyzed arylation of arene C-H bonds. , 2008, Journal of the American Chemical Society.

[35]  Chang-Liang Sun,et al.  Palladium-catalyzed direct arylation of (hetero)arenes with aryl boronic acids. , 2008, Angewandte Chemie.

[36]  Brenton DeBoef,et al.  C-C bond formation via double C-H functionalization: aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls. , 2007, Organic letters.

[37]  B. Kumar,et al.  Synthesis of benzofuran scaffold-based potential PTP-1B inhibitors. , 2007, Bioorganic & medicinal chemistry.

[38]  Y. Aoyagi,et al.  Palladium-catalyzed arylation of furan, thiophene, benzo[b]furan and benzo[b]thiophene , 1990 .