Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands.

scientific article

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands. is …
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scholarly articleQ13442814

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P356DOI10.1021/AR800036S
P7916Mendeley publication ID9ca6a78b-0f2c-3b67-a7cb-7b168e9a4726
P932PMC publication ID2645945
P698PubMed publication ID18620434
P5875ResearchGate publication ID5231002

P50authorStephen L. BuchwaldQ6134174
Ruben MartinQ39185602
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Distinct mechanisms for the oxidative addition of chloro-, bromo-, and iodoarenes to a bisphosphine palladium(0) complex with hindered ligandsQ46482798
Brønsted acid-catalyzed allylboration: short and stereodivergent synthesis of all four eupomatilone diastereomers with crystallographic assignmentsQ46700519
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General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in WaterQ57406375
Access to Guaianolides: Highly Efficient Stereocontrolled Total Synthesis of (±)-GeigerinQ57406377
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Stereospecific palladium-catalyzed cross-coupling of (E)- and (Z)-alkenylsilanolates with aryl chloridesQ79430077
Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and estersQ79841173
3-boryl-2,2'-bithiophene as a versatile core skeleton for full-color highly emissive organic solidsQ80011370
Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygenQ80048066
Transition-metal-catalyzed reactions in heterocyclic synthesisQ80073280
Suzuki cross-coupling on enantiomerically pure epoxides: efficient synthesis of diverse, modular amino alcohols from single enantiopure precursorsQ80084543
The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofuransQ80117243
Easily accessible and highly tunable indolyl phosphine ligands for Suzuki-Miyaura coupling of aryl chloridesQ80549328
Electronic effects on the selectivity of pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: the competitive roles of amine binding and acidityQ80752486
A general method for the direct alpha-arylation of aldehydes with aryl bromides and chloridesQ80849404
Dynamic kinetic resolution of alpha,beta-unsaturated lactones through asymmetric copper-catalyzed conjugate reduction: application to the total synthesis of eupomatilone-3Q81134329
Monoligated palladium species as catalysts in cross-coupling reactionsQ81209998
Insights into amine binding to biaryl phosphine palladium oxidative addition complexes and reductive elimination from biaryl phosphine arylpalladium amido complexes via density functional theoryQ81237847
Conjugated polymers and aromaticityQ81338642
Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reactionQ81875528
Microwave-assisted intramolecular Suzuki-Miyaura reaction to macrocycle, a concise asymmetric total synthesis of biphenomycin BQ81907315
Evidence for the formation and structure of palladacycles during Pd-catalyzed C-N bond formation with catalysts derived from bulky monophosphinobiaryl ligandsQ82100543
A Convenient and General Method for Pd-Catalyzed Suzuki Cross-Couplings of Aryl Chlorides and Arylboronic AcidsQ88520152
The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the articleQ95391495
P433issue11
P407language of work or nameEnglishQ1860
P921main subjectpalladiumQ1089
P304page(s)1461-1473
P577publication date2008-11-01
P1433published inAccounts of Chemical ResearchQ899474
P1476titlePalladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands
P478volume41

Reverse relations

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Q90322992Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling
Q92927232Photo-Assisted Synthesis of a Pd-Ag@CQD Nanohybrid and Its Catalytic Efficiency in Promoting the Suzuki-Miyaura Cross-Coupling Reaction under Ligand-Free and Ambient Conditions
Q41473855Photooxidation of mixed aryl and biarylphosphines
Q50079246Photophysical properties of three coordinated copper(i) complexes bearing 1,10-phenanthroline and a monodentate phosphine ligand
Q35837837Photostabilizing Efficiency of PVC in the Presence of Schiff Bases as Photostabilizers.
Q45752508Phthalide: a direct building-block towards P,O and P,N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides
Q92939467Poly(tetrafluoroethylene)-Stabilized Metal Nanoparticles: Preparation and Evaluation of Catalytic Activity for Suzuki, Heck, and Arene Hydrogenation in Water
Q53413990Preparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability.
Q48280296Preparation and catalytic performance of a molecularly imprinted Pd complex catalyst for Suzuki cross-coupling reactions.
Q48321078Preparation of Solid Polyfunctional Alkynylzinc Pivalates with Enhanced Air and Moisture Stability for Organic Synthesis
Q36886883Probing the role of the vancomycin e-ring aryl chloride: selective divergent synthesis and evaluation of alternatively substituted E-ring analogues
Q82321361PC–N-Heterocycles: synthesis of biaryl-type 1,3-benzazaphospholes with ortho-substituted phenyl or 2-heteroaryl groups
Q55099746QuadraPure-supported palladium nanocatalysts for microwave-promoted Suzuki cross-coupling reaction under aerobic condition.
Q48231493Quantifying and understanding the steric properties of N-heterocyclic carbenes
Q47636290R/X exchange reactions in cis-[M(R)2{P(X)(NMeCH2)2}2] (M = Pd, Pt), via a phosphenium intermediate.
Q48234906Radical Arylation of Anilines and Pyrroles via Aryldiazotates
Q55021811Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies.
Q45999496Rapid microwave-assisted sol-gel preparation of Pd-substituted LnFeO3 (Ln = Y, La): phase formation and catalytic activity.
Q33533417Rational exploration of N-heterocyclic carbene (NHC) palladacycle diversity: a highly active and versatile precatalyst for Suzuki-Miyaura coupling reactions of deactivated aryl and alkyl substrates
Q53592076Regioselective electrophilic aromatic bromination: theoretical analysis and experimental verification.
Q42388442Replacement of the Bryostatin A- and B-Pyran Rings With Phenyl Rings Leads to Loss of High Affinity Binding With PKC.
Q62552822Resorcinarenyl-Phosphines in Suzuki-Miyaura Cross-Coupling Reactions of Aryl Chlorides
Q51161440Rhodium(iii)-catalyzed ortho-olefination of aryl phosphonates.
Q36088737Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes
Q59222844Rhodium/N-Heterocyclic Carbene Catalyzed Direct Intermolecular Arylation of sp2and sp3CH Bonds with Chelation Assistance
Q36765746STILLE CROSS-COUPLING REACTIONS OF ARYL MESYLATES AND TOSYLATES USING A BIARYLPHOSPHINE BASED CATALYST SYSTEM.
Q38148935Selection of boron reagents for Suzuki-Miyaura coupling.
Q41775816Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters
Q41838519Selectivity, Compatibility, Downstream Functionalization, and Silver Effect in the Gold and Palladium Dual-Catalytic Synthesis of Lactones
Q39105672Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis.
Q45356636Silyl-protected dioxaborinanes: application in the Suzuki cross-coupling reaction
Q41761401Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling
Q38815720Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes.
Q92931589Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki-Miyaura Coupling Reactions
Q92134201Solid-state Suzuki-Miyaura cross-coupling reactions: olefin-accelerated C-C coupling using mechanochemistry
Q58750250Some mechanistic aspects regarding the Suzuki-Miyaura reaction between selected -substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine
Q50077644Sonogashira (Cu and amine free) and Suzuki coupling in air catalyzed via nanoparticles formed in situ from Pd(ii) complexes of chalcogenated Schiff bases of 1-naphthaldehyde and their reduced forms
Q46320831Spectroscopic characterization of (diiodomethyl)zinc iodide: application to the stereoselective synthesis and functionalization of iodocyclopropanes
Q46475715Stability and Unimolecular Reactivity of Palladate(II) Complexes [Ln PdR3 ](-) (L=Phosphine, R=Organyl, n=0 and 1).
Q36036205Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes.
Q36470436Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling
Q42408294Stereoretentive Suzuki-Miyaura coupling of haloallenes enables fully stereocontrolled access to (-)-peridinin
Q43239796Stereoselective synthesis of beta-chlorovinyl ketones and arenes by the catalytic addition of acid chlorides to alkynes.
Q41169168Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity
Q41983862Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P-(+)-dispegatrine and six other monomeric indole alkaloids
Q42404427Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates
Q89040323Straightforward Synthesis of Bifunctional Phosphorus Phenols via Phosphination of In Situ Generated o-Quinone Methides
Q50874845Structurally versatile phosphine and amine donors constructed from N-heterocyclic olefin units.
Q42336569Structure-activity studies of non-steroid analogues structurally-related to neuroprotective estrogens
Q50073813Sub-nanometre metal clusters for catalytic carbon-carbon and carbon-heteroatom cross-coupling reactions
Q58829167Substituted triphenylamines as building blocks for star shaped organic electronic materials
Q35836362Suzuki coupling of potassium cyclopropyl- and alkoxymethyltrifluoroborates with benzyl chlorides
Q46403875Suzuki-Miyaura Cross-Coupling Reactions of Highly Fluorinated Arylboronic Esters: Catalytic Studies and Stoichiometric Model Reactions on the Transmetallation Step.
Q37253987Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation
Q37441389Suzuki-Miyaura cross-coupling optimization enabled by automated feedback
Q34502010Synthesis and Biological Evaluation of Lactimidomycin and Its Analogues.
Q64028507Synthesis and Characterisation of 1,7-Di- and Inherently Chiral 1,12-Di- and 1,6,7,12-Tetraarylperylenetetracarbox-3,4:9,10-diimides
Q46502342Synthesis and catalytic application of palladium nanoparticles supported on kaolinite-based nanohybrid materials
Q35763325Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides
Q87388353Synthesis and resolution of the biaryl-like diphosphine (S)-Me2-CATPHOS, preparation of a derived rhodium precatalyst and applications in asymmetric hydrogenation
Q89659361Synthesis of Bisphenol Neolignans Inspired by Honokiol as Antiproliferative Agents
Q42333844Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins.
Q87388350Synthesis of an electron-rich KITPHOS monophosphine, preparation of derived metal complexes and applications in catalysis
Q37155508Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
Q52782591Synthesis of chiral heterocycles by ligand-controlled regiodivergent and enantiospecific Suzuki Miyaura cross-coupling.
Q47996378Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water
Q53559735Tandem Oxidative C-H Amination and Iodization to Synthesize Difunctional Atropoisomeric P-Stereogenic Phosphinamides.
Q48303245The 2010 Chemistry Nobel Prize to R.F. Heck, E. Negishi, and A. Suzuki for palladium-catalyzed cross-coupling reactions
Q53468947The effects of CO2 pressure and pH on the Suzuki coupling of basic nitrogen containing substrates.
Q36189584The vinylogous aldol reaction of unsaturated esters and enolizable aldehydes using the novel Lewis acid aluminum tris(2,6-di-2-naphthylphenoxide)
Q37737101Theoretical aspects of palladium-catalysed carbon-carbon cross-coupling reactions
Q57786622Through the Maze: Cross-Coupling Pathways to a Helical Hexaphenyl “Geländer” Molecule
Q42723519Topological Control of Columnar Stacking Made of Liquid-Crystalline Thiophene-Fused Metallonaphthalocyanines
Q35775905Total Synthesis of (-)-Nodulisporic Acid D.
Q89441992Total Synthesis of (±)-Exotine B
Q56689760Toward Generalization of Iterative Small Molecule Synthesis
Q35049991Transition metal-catalyzed decarboxylative allylation and benzylation reactions
Q48283524Transition-Metal-Catalyzed Selective Cage B-H Functionalization of o-Carboranes.
Q48206070Triazole-Containing Dendrimer-like Core Cross-Linked Micelles that Stabilize Pd Nanoparticles as Heterogenized Homogeneous Catalysts for Room-Temperature Suzuki-Miyaura Reactions in Water
Q46953212Tripod immobilization of triphenylphosphane on a silica-gel surface to enable selective mono-ligation to palladium: application to Suzuki-Miyaura cross-coupling reactions with chloroarenes.
Q48715136Ultrasonic assisted synthesis of palladium-nickel/iron oxide core-shell nanoalloys as effective catalyst for Suzuki-Miyaura and p-nitrophenol reduction reactions.
Q37329354Use of potassium beta-trifluoroborato amides in Suzuki-Miyaura cross-coupling reactions
Q91174736Visible-Light-Enhanced Suzuki-Miyaura Reactions of Aryl Chlorides in Water with Pd NPs Supported on a Conjugated Nanoporous Polycarbazole
Q46877522Visible-light-enhanced Suzuki-Miyaura coupling reaction by cooperative photocatalysis with an Ru-Pd bimetallic complex
Q60389773Water-Soluble Palladium(II) Sulfonated Thiosemicarbazone Complexes: Facile Synthesis and Preliminary Catalytic Studies in the Suzuki-Miyaura Cross-Coupling Reaction in Water
Q46775953Water-stabilized three- and four-atom palladium clusters as highly active catalytic species in ligand-free C-C cross-coupling reactions
Q89641541Well-defined nickel and palladium precatalysts for cross-coupling
Q58738547What makes for a good catalytic cycle? A theoretical study of the SPhos ligand in the Suzuki–Miyaura reaction
Q58878081When Chirality Meets “Buchwald-Type” Phosphines: Synthesis and Evaluation in Frustrated Lewis Pair-, Lewis Base- and Palladium-Promoted Asymmetric Catalysis
Q35184482γ-Selective cross-coupling of allylic silanolate salts with aromatic bromides using trialkylphosphonium tetrafluoroborate salts prepared directly from phosphine•borane adducts.