Achievement of regioselectivity in transition metal-catalyzed direct C–H (hetero)arylation reactions of heteroarenes with one heteroatom through the use of removable protecting/blocking substituents or traceless directing groups. Issue 15 (14th April 2016)

• Record Type: Journal Article
• Authors: Rossi, Renzo; Lessi, Marco; Manzini, Chiara; Marianetti, Giulia; Bellina, Fabio
• Is Part Of: Tetrahedron. Volume 72:Issue 15(2016)
• Page Start: 1795
• Page End: 1837
• Publication Date: 2016-04-14
• Subjects: Chemoselectivity -- Regioselectivity -- Direct C–H (hetero)arylation -- Transition metal catalysts -- Removable groups -- Traceless directing groups -- Deprotection; Ac acetyl -- acac acetylacetonate -- 1-Ad 1-adamantyl -- AIBN azobisisobutyronitrile -- Ar aryl -- Boc tert-butoxycarbonyl -- BQ 1, 4-benzoquinone -- n-Bu n-butyl -- t-Bu t-butyl -- ∗Cp cyclopentadienyl -- Cy cyclohexyl -- DBU 1, 5-diazabicyclo[5.4.0]undec-7-ene -- DCE 1, 2-dichloroethane -- DFT density functional theory -- DMEDA N, N-dimethylethylenediamine -- dppb 1, 4-bis(diphenylphosphino)butane -- DMA N, N-dimethylacetamide -- DMAP 4-dimethylaminopyridine -- DMF N, N-dimethylformamide -- DMSO dimethylsulfoxide -- dtbpy 4, 4′-di-tert-butyl-2, 2′-dipyridyl -- Et ethyl -- HetAr heteroaryl -- n-Hex n-hexyl -- LDA lithium diisopropylamide -- Me methyl -- JohnPhos (2-di-tert-butylphosphino)biphenyl -- LiTMP lithium tetramethylpiperidide -- MS molecular sieves -- NMP N-methyl-2-pyrrolidone -- i-Pr i-propyl -- Py pyridine -- rt room temperature -- SEM 2-(trimethylsilyl)ethoxymethyl -- TBAB tetra-n-butyl bromide -- TBAF tetra-n-butyl fluoride -- TEMPO (2, 2, 6, 6-tetramethylpiperidin-1-yl)oxyl -- Tf trifluoromethanesulfonyl -- Tfa trifluoroacetate -- THF tetrahydrofuran -- TIPS triisopropylsilyl -- XPhos 2-dicyclohexylphosphino-2′, 4′, 6′-triisopropylbiphenyl; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.02.037
• Languages: English
• ISSNs: 0040-4020

Abstract

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