Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions

scientific article

Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions is …
instance of (P31):
scholarly articleQ13442814

External links are
P356DOI10.1021/JA1086485
P932PMC publication ID3075889
P698PubMed publication ID21114321
P5875ResearchGate publication ID49642087

P50authorRobert PatonQ19862676
Kendall HoukQ6388913
P2093author name stringG-Yoon J Im
Neil K Garg
Paul H-Y Cheong
Sarah M Bronner
Adam E Goetz
P2860cites workIndolynes as electrophilic indole surrogates: fundamental reactivity and synthetic applicationsQ83261139
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron densityQ21708802
Indolyne and aryne distortions and nucleophilic regioselectivitesQ33640922
New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library developmentQ34154522
Experimental and theoretical investigations into the unusual regioselectivity of 4,5-, 5,6-, and 6,7-indole aryne cycloadditionsQ34248018
Regioselective Diels-Alder cycloadditions and other reactions of 4,5-, 5,6-, and 6,7-indole arynes.Q34271355
Semiempirical hybrid density functional with perturbative second-order correlationQ34488458
One century of aryne chemistryQ34531060
Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivityQ34660852
Cancer chemotherapy and heterocyclic compoundsQ34673516
The combinatorial synthesis of bicyclic privileged structures or privileged substructures.Q35083549
Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acidsQ37063610
Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azidesQ37112585
Concise total synthesis of (+/-)-cis-trikentrin A and (+/-)-herbindole A via intermolecular indole aryne cycloadditionQ37297194
From nature to drug discovery: the indole scaffold as a 'privileged structure'.Q37516118
Catalytic functionalization of indoles in a new dimensionQ37641200
Cycloaddition reactions of butadiene and 1,3-dipoles to curved arenes, fullerenes, and nanotubes: theoretical evaluation of the role of distortion energies on activation barriersQ43251992
Novel sulfonate analogues of combretastatin A-4: potent antimitotic agentsQ43569141
The first total synthesis of dragmacidin d.Q44197878
Benchmarking the Conductor-like Polarizable Continuum Model (CPCM) for Aqueous Solvation Free Energies of Neutral and Ionic Organic Molecules.Q46022485
The direct acyl-alkylation of arynesQ46189940
Transition state distortion energies correlate with activation energies of 1,4-dihydrogenations and Diels-Alder cycloadditions of aromatic moleculesQ46402510
Substitution of hydroxybiaryls via directed ortho-lithiation of N-silylated O-aryl N-isopropylcarbamatesQ46668900
Theory of 1,3-dipolar cycloadditions: distortion/interaction and frontier molecular orbital modelsQ46792442
A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congenersQ46898564
CO2 incorporation reaction using arynes: straightforward access to benzoxazinone.Q51142191
Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model.Q52019488
Hetarine, XIV1) Über die Selektivität hetero- und carbocyclischer Arine gegenüber BasenQ59650173
Pi-nucleophilicity in carbon-carbon bond-forming reactionsQ78814938
Strain-Induced Regioselectivities in Reactions of Benzyne Possessing a Fused Four-Membered RingQ79079690
Direct C-arylation of beta-enamino esters and ketones with arynesQ79797084
Rapid synthesis of the N-methylwelwitindolinone skeletonQ80945305
Facile deallylation protocols for the preparation of N-unsubstituted triazoles and tetrazolesQ80951424
Indole-derived arynes and their Diels-Alder reactivity with furansQ81321413
Copper-free 'click': 1,3-dipolar cycloaddition of azides and arynesQ82965262
P433issue50
P407language of work or nameEnglishQ1860
P304page(s)17933-17944
P577publication date2010-11-29
P1433published inJournal of the American Chemical SocietyQ898902
P1476titleIndolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions
P478volume132

Reverse relations

cites work (P2860)
Q649265711,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.
Q344710465-Hydroxyindoles by intramolecular alkynol-furan diels-alder cycloaddition
Q37714083A homologation approach to the synthesis of difluorinated cycloalkynes
Q49692344A study on an unusual SN2 mechanism in the methylation of benzyne through nickel-complexation.
Q51349192Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes.
Q41590341An efficient computational model to predict the synthetic utility of heterocyclic arynes
Q39266241Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model
Q33930778Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries
Q88534461Arynes and Cyclic Alkynes as Synthetic Building Blocks for Stereodefined Quaternary Centers
Q58878100Atroposelective synthesis of axially chiral P,S-ligands based on arynes
Q34731126Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates
Q35744932Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C-H Activation and Orthogonal Reactivity.
Q55447796C4-H indole functionalisation: precedent and prospects.
Q35664278Computational predictions of substituted benzyne and indolyne regioselectivities
Q40432608Concise Synthesis of Functionalized Benzocyclobutenones
Q37262182Cycloaddition of Arynes and Cyclic Enol Ethers as a Platform for Access to Stereochemically Defined 1,2-Disubstituted Benzocyclobutenes
Q34392432Cycloadditions of cyclohexynes and cyclopentyne
Q41806928Direct intermolecular aniline ortho-arylation via benzyne intermediates
Q42084097Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols
Q43775392Electrophilicity: the "dark-side" of indole chemistry
Q37481295Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.
Q46106780Expanding the ROMP Toolbox: Synthesis of Air-Stable Benzonorbornadiene Polymers by Aryne Chemistry
Q44445147Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes
Q34489853General method for functionalized polyaryl synthesis via aryne intermediates.
Q35852057Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles
Q39515597Hardness potential derivatives and their relation to Fukui indices.
Q34282744Mechanism of the reactions of alcohols with o-benzynes
Q42117552Overturning indolyne regioselectivities and synthesis of indolactam V
Q33760319Quantification of the Electrophilicity of Benzyne and Related Intermediates
Q42225085Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes
Q36011672Reactivity of biarylazacyclooctynones in copper-free click chemistry
Q36492950Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model
Q34266099Regioselectivity of Diels-Alder Reactions Between 6,7-Dehydrobenzofuran and 2-Substituted Furans
Q50901595Selective S-arylation of 2-oxazolidinethiones and selective N-arylation of 2-benzoxazolinones/2-benzimidazolinones.
Q36241930Steric effects compete with aryne distortion to control regioselectivities of nucleophilic additions to 3-silylarynes
Q92783708Synthesis of Uracil-Iodonium(III) Salts for Practical Utilization as Nucleobase Synthetic Modules
Q43110829The hexadehydro-Diels-Alder reaction: a new chapter in aryne chemistry.
Q64901742The mechanism of the triple aryne-tetrazine reaction cascade: theory and experiment.
Q34458865The role of aryne distortions, steric effects, and charges in regioselectivities of aryne reactions
Q46497159Thiazolobenzyne: a versatile intermediate for multisubstituted benzothiazoles.
Q34266054Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling
Q33604000Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2.
Q46391638Total syntheses of the elusive welwitindolinones with bicyclo[4.3.1] cores
Q35139432Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin families
Q38642499Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate
Q42866918Transition-metal-free alkynylation of aryl chlorides
Q54692806ortho-Selective nucleophilic addition of amines to 3-borylbenzynes: synthesis of multisubstituted anilines by the triple role of the boryl group.

Search more.