Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes

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Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1021/JA306723R
P8608Fatcat IDrelease_vxz7rwighnaj5hjxf53s233c54
P932PMC publication ID3445038
P698PubMed publication ID22876797

P50authorKendall HoukQ6388913
P2093author name stringNeil K Garg
Sarah M Bronner
Joel L Mackey
P2860cites workIndolyne and aryne distortions and nucleophilic regioselectivitesQ33640922
One century of aryne chemistryQ34531060
Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivityQ34660852
Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additionsQ34788171
Reactivity and regioselectivity in 1,3-dipolar cycloadditions of azides to strained alkynes and alkenes: a computational studyQ34982330
A novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition and its application in the synthesis of the cortistatin coreQ37005614
Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acidsQ37063610
Diels-Alder exo selectivity in terminal-substituted dienes and dienophiles: experimental discoveries and computational explanationsQ37083930
Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azidesQ37112585
Theoretical bond dissociation energies of halo-heterocycles: trends and relationships to regioselectivity in palladium-catalyzed cross-coupling reactionsQ37314298
Use of solution-phase vibrational frequencies in continuum models for the free energy of solvationQ37923477
A comprehensive history of arynes in natural product total synthesisQ37996475
Overturning indolyne regioselectivities and synthesis of indolactam VQ42117552
Stereoinduction by distortional asymmetryQ42788109
Enantioselective, thiourea-catalyzed intermolecular addition of indoles to cyclic N-acyl iminium ionsQ42941441
Origin of regioselectivity in palladium-catalyzed cross-coupling reactions of polyhalogenated heterocyclesQ46175568
Synthesis of biaryl compounds through three-component assembly: ambidentate effect of the tert-butyldimethylsilyl group for regioselective Diels-Alder and Hiyama coupling reactionsQ46379721
Transition state distortion energies correlate with activation energies of 1,4-dihydrogenations and Diels-Alder cycloadditions of aromatic moleculesQ46402510
Theory of 1,3-dipolar cycloadditions: distortion/interaction and frontier molecular orbital modelsQ46792442
Synthesis of indazoles by the [3+2] cycloaddition of diazo compounds with arynes and subsequent acyl migrationQ46859994
Modular approach to silicon-bridged biaryls: palladium-catalyzed intramolecular coupling of 2-(arylsilyl)aryl triflatesQ47250302
Approaches to the quaternary stereocentre and to the heterocyclic core in diazonamide A using the Heck reaction and related coupling reactions.Q50696292
The activation strain model of chemical reactivityQ62109526
Direct C-arylation of beta-enamino esters and ketones with arynesQ79797084
Regioselective reactions of highly substituted arynesQ82952369
Copper-free 'click': 1,3-dipolar cycloaddition of azides and arynesQ82965262
Regioselective synthesis of 3-(2-hydroxyaryl)pyridines via arynes and pyridine N-oxidesQ83912983
ortho-Selective nucleophilic addition of primary amines to silylbenzynes: synthesis of 2-silylanilinesQ84071628
P433issue34
P407language of work or nameEnglishQ1860
P304page(s)13966-13969
P577publication date2012-08-15
P1433published inJournal of the American Chemical SocietyQ898902
P1476titleSteric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes
P478volume134

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