Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.

No abstract is available for this paper.

• Publication year

  2014

• Venue

  Angewandte Chemie

• Publication date

  2014-02-10

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.201310149PMID 24446067PMCID PMC3970409
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Decarbonylative C-C bond forming reactions mediated by transition metals

  2013cited by this paper
• Rh(I)-catalyzed decarbonylation of diynones via C-C activation: orthogonal synthesis of conjugated diynes.

  2013cited by this paper
• Rhodium-catalyzed C-C Bond Cleavage Reactions - An Update

  2012cited by this paper
• Highly enantioselective Rh-catalyzed carboacylation of olefins: efficient syntheses of chiral poly-fused rings.

  2012cited by this paper
• Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

  2012cited by this paper
• Rhodium-catalyzed regioselective carboacylation of olefins: a C-C bond activation approach for accessing fused-ring systems.

  2012cited by this paper
• Extrusion of CO from aryl ketones: rhodium(I)-catalyzed C-C bond cleavage directed by a pyridine group.

  2012cited by this paper
• Transition-Metal-Mediated Cleavage and Activation of C–C Single Bonds

  2012cited by this paper
• Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

  2011cited by this paper
• Cyclobutane in der Katalyse

  2011cited by this paper
• Metal-catalysed cleavage of carbon-carbon bonds.

  2011cited by this paper
• Cyclobutanes in catalysis.

  2011cited by this paper
• Selected Synthetic Strategiesto Spirocyclics

  2009cited by this paper
• C–H Bond Formation: Through Isomerization

  2007cited by this paper
• Directed C – C Bond Activation by Transition Metal Complexes

  2007cited by this paper
• Rhodium-Catalyzed C-C Bond Cleavage Reactions

  2007cited by this paper
• Electronic effects on reductive elimination to form carbon-carbon and carbon-heteroatom bonds from palladium(II) complexes.

  2007cited by this paper
• Activation of a Cyclobutanone Carbon–Carbon Bond over an Aldehyde Carbon–Hydrogen Bond in the Rhodium-catalyzed Decarbonylation

  2006cited by this paper
• Convergent Synthesis of Azabicycloalkenones using Squaric Acid as Platform

  2006cited by this paper
• Ruthenium-catalyzed Reconstructive Synthesis of Functional Organic Molecules via Cleavage of Carbon–Carbon Bonds

  2005cited by this paper
• Ru- and Rh-catalyzed C-C bond cleavage of cyclobutenones: reconstructive and selective synthesis of 2-pyranones, cyclopentenes, and cyclohexenones.

  2004cited by this paper
• Transition metal-catalyzed carbon-carbon bond activation.

  2004cited by this paper
• Direct oxidative Heck cyclizations: intramolecular Fujiwara-Moritani arylations for the synthesis of functionalized benzofurans and dihydrobenzofurans.

  2004cited by this paper
• Catalytic C-H bond functionalization with palladiumII: aerobic oxidative annulations of indoles.

  2003cited by this paper
• Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex.

  2003cited by this paper
• Cyclometalated phosphine-based pincer complexes: mechanistic insight in catalysis, coordination, and bond activation.

  2003cited by this paper
• Catalyzed intramolecular olefin insertion into a carbon-carbon single bond.

  2002cited by this paper
• Cleavage of the carbon–carbon bond in biphenylene using transition metals

  2002cited by this paper
• Ruthenium-Catalyzed Reconstructive Synthesis of Cyclopentenones by Unusual Coupling of Cyclobutenediones with Alkenes Involving Carbon−Carbon Bond Cleavage

  2000cited by this paper
• Metallinsertion in C-C-Bindungen in Lösung

  1999cited by this paper
• Cleavage of Carbon—Carbon Single Bonds by Transition Metals

  1999cited by this paper
• Metal Insertion into C-C Bonds in Solution.

  1999cited by this paper
• Stereocontrolled synthesis of spirocyclics

  1999cited by this paper
• CHIRAL PHOSPHANYLDIHYDROOXAZOLES IN ASYMMETRIC CATALYSIS : ENANTIOSELECTIVE HECK REACTIONS

  1996cited by this paper
• Breaking of the C−C Bond of Cyclobutanones by Rhodium(I) and Its Extension to Catalytic Synthetic Reactions

  1996cited by this paper
• Chirale Phosphanyldihydrooxazole in der asymmetrischen Katalyse: enantioselektive Heck‐Reaktionen

  1996cited by this paper
• Selective activation of carbon–carbon bonds next to a carbonyl group

  1994cited by this paper
• Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran with phenyl triflate. A novel asymmetric catalysis involving a kinetic resolution process

  1993cited by this paper
• The fall of the C-C bond

  1993cited by this paper
• The organometallic chemistry of alkanes

  1985cited by this paper
• Selective conformational changes of cyclic systems—XII: Enhanced reactivity of ten membered ring ketones due to transanular steric compression: hydrates and hemiketals from oxo-[2.2]metacyclophanes

  1980cited by this paper
• DECARBONYLATION OF α-AND β-DIKETONES CATALYZED BY RHODIUM COMPOUNDS

  1974cited by this paper

• Computational Exploration of Intramolecular Cycloaddition of Cyclobutanone with Alkene Catalyzed by Rhodium Versus Nickel: The Origins of Selectivities.

  2025cites this paper
• Catalytic asymmetric intermolecular [4 + 2] annulation of benzocyclobutenones with Alkynes and activated carbonyls via C—C activation

  2025cites this paper
• Aza-[4 + 2]-cycloaddition of benzocyclobutenones into isoquinolinone derivatives enabled by photoinduced regio-specific C–C bond cleavage

  2024cites this paper
• Catalytic [4+2]- and [4+4]-cycloaddition using furan-fused cyclobutanone as a privileged C4 synthon

  2024cites this paper
• Type I [4σ + 4π] vs [4σ + 4π - 1] Cycloadditions Accessing Medium-Sized Carbocycles and Discovery of a Liver X Receptor β-Selective Ligand.

  2024cites this paper
• Ligand-Controlled Nickel-Catalyzed Reactions of Benzocyclobutenones with Alkynyltrifluoroborates: Diverse Construction of Polysubstituted Naphthols.

  2023cites this paper
• Site-Selective C-C Cleavage of Benzocyclobutenones Enabled by a Blocking Strategy via Ni Catalysis.

  2021cites this paper
• Skeleton Reorganization of Substituted Benzocyclobutenols through Rh-Catalyzed C-C Bond Cleavage Manipulated by Hydrogen Transfer.

  2021cites this paper
• Decarbonylative Issues Involved in Ru(II)‐Catalyzed [6+2−1] Annulation Reaction of Hydroxychromone with Alkyne: A DFT Study

  2021cites this paper
• Ru(ii)-Catalyzed cascade decarbonylative annulation and dehydrogenative alkenylation reactions: synthesis of phthalides.

  2021cites this paper
• Csp–Csp bond cleavage and fragment coupling: a transition metal-free “extrusion and recombination” approach towards synthesis of 1,2-diketones

  2021cites this paper
• Recent advances in decarbonylative annulation reactions.

  2021cites this paper
• Rh-Catalyzed Cascade C–C/Colefin–H Activations and Mechanistic Insight

  2021cites this paper
• Carbon‒Carbon Bond Activation of Ketones

  2020cites this paper
• decarbonylative spirocyclization

  2020cites this paper
• Divergent Coupling of Benzocyclobutenones with Indoles via C−H and C−C Activations

  2020cites this paper
• Pd‐Catalyzed Regio‐ and Diastereoselective Heck Cyclization to Access Bicyclo[3.2.1]octanone Ring Systems

  2020cites this paper
• Divergent Coupling of Benzocyclobutenones with Indoles via C-H and C-C Activations.

  2020cites this paper
• Copper-catalyzed cascade cyclization reaction of 3-aminocyclobutenones with electron-deficient internal alkynes: synthesis of fully substituted indoles.

  2020cites this paper
• Selective Decarbonylation via Transition-Metal-Catalyzed Carbon-Carbon Bond Cleavage.

  2020cites this paper
• Synthesis of Concave and Vaulted 2H-Pyran-fused BINOLs and Corresponding [5] & [7]-Oxa-helicenoids: Regioselective Cascade Concerted Route and DFT studies.

  2020cites this paper
• Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis

  2020cites this paper
• Total Synthesis of Galanthamine and Lycoramine Featuring an Early-Stage C-C and a Late-Stage Dehydrogenation via C-H Activation.

  2020cites this paper
• Cu-Catalyzed Denitrogenative Transannulation of 3-Aminoindazoles To Assemble 1-Aminoisoquinolines and 3-Aminobenzothiophenes.

  2019cites this paper
• Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction.

  2019cites this paper
• Mechanistic insights into intermolecular cyclization of ring-fused benzocyclobutenols with alkynes catalyzed by [{Ir(OMe)COD}2]

  2019cites this paper
• Total synthesis of penta-Me amurensin H and diptoindonesin G featuring a Rh-catalyzed carboacylation/aromatization cascade enabled by C C activation

  2019cites this paper
• Rhodium(I)-Catalyzed Reactions via Carbon-Carbon Bond Cleavage

  2019cites this paper
• Nickel‐Catalyzed Intramolecular Coupling of Sulfones via the Extrusion of Sulfur Dioxide

  2019cites this paper
• Tunable Functionalization of Saturated C-C and C-H Bonds of N,N'-Diarylpiperazines Enabled by tert-Butyl Nitrite (TBN) and NaNO2 Systems.

  2019cites this paper
• Rh-Catalyzed intramolecular decarbonylative cyclization of ortho-formyl group tethered alkylidenecyclopropanes (ACPs) for the construction of 2-methylindenes

  2019cites this paper
• Rh(I)-catalyzed ring-opening of cyclobutanols via C–C bond activation: Synthesis of cis-olefin with a remote aldehyde

  2019cites this paper
• Copper-Mediated Deacylative Coupling of Ynones via C-C Bond Activation under Mild Conditions.

  2019cites this paper
• Oxidative Addition Promoted C–C Bond Cleavage in Rh-Mediated Cyclopropenone Activation: A DFT Study

  2019cites this paper
• Catalytic Enantioselective Synthesis of 3,4-Polyfused Oxindoles with Quaternary All-Carbon Stereocenters: A Rh-Catalyzed C-C Activation Approach.

  2018cites this paper
• Rhodium(I)-Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C-C Activation of Benzocyclobutenones.

  2018cites this paper
• Rhodium(iii)-catalysed decarbonylative annulation through C-H activation: expedient access to aminoisocoumarins by weak coordination.

  2018cites this paper
• Expeditious Synthesis of Isoquinolone Derivatives by Rhodium(I)-Catalyzed Annulation Reaction through C-C Bond Cleavage.

  2018cites this paper
• Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols.

  2018cites this paper
• Activation and recyclization of a benzocyclobutenone derivative catalyzed by a chiral Rh(I) complex based on DFT investigations

  2018cites this paper
• Cobalt-Catalyzed Intramolecular Alkyne/Benzocyclobutenone Coupling: C-C Bond Cleavage via a Tetrahedral Dicobalt Intermediate.

  2018cites this paper
• Lewis acid catalyzed asymmetric [4+2] cycloaddition of cyclobutenones to synthesize α,β-unsaturated δ-lactones.

  2018cites this paper
• Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction.

  2018cites this paper
• Synthetic Approach to Benzocyclobutenones Using Visible Light and a Phosphonate Auxiliary.

  2018cites this paper
• Three-Component Oxyarylation of Alkenes Enables Access to C3-Substituted Dihydrobenzofurans.

  2018cites this paper
• Mechanism and Origins of the Chemo- and Regioselectivities in Nickel-Catalyzed Intermolecular Cycloadditions of Benzocyclobutenones with 1,3-Dienes.

  2017cites this paper
• Recent Methodologies That Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes.

  2017cites this paper
• Characterization of the RhI /dppe-Catalyzed Ring Expansion of 2-Alkyl-Benzocyclobutenones by DFT Calculations.

  2017cites this paper
• C-C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and Application in the Assembly of Polycyclic Aromatic Hydrocarbons.

  2017cites this paper
• σ N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines.

  2017cites this paper
• Mechanistic investigation of Rh(I)-catalyzed alkyne–isatin decarbonylative coupling

  2017cites this paper
• A Two-Step Synthesis of 2-Spiropiperidines.

  2017cites this paper
• Rhodium(i)-catalysed skeletal reorganisation of benzofused spiro[3.3]heptanes via consecutive carbon-carbon bond cleavage.

  2016cites this paper
• All-carbon quaternary centers in natural products and medicinal chemistry: recent advances

  2016cites this paper
• Ruthenium‐ and Rhodium‐Catalyzed Strain‐Driven Cleavage and Reconstruction of the C–C Bond

  2016cites this paper
• Synthesis of Multisubstituted Silyloxy‐based Donor‐Acceptor Cyclobutanes by an Acid‐Catalyzed [2+2] Cycloaddition

  2016cites this paper
• Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C-N Bond Activation.

  2016cites this paper
• Synthesis and applications of rhodacyclopentanones derived from C-C bond activation.

  2016cites this paper
• Enantioselective Rh-Catalyzed Carboacylation of C═N Bonds via C-C Activation of Benzocyclobutenones.

  2016cites this paper
• Potential of Metal-Catalyzed C-C Single Bond Cleavage for Organic Synthesis.

  2016cites this paper
• Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.

  2016cites this paper
• Synthesis of Multiply Substituted Polycyclic Aromatic Hydrocarbons by Iridium-Catalyzed Annulation of Ring-Fused Benzocyclobutenol with Alkyne through C-C Bond Cleavage.

  2016cites this paper
• Theoretical Study of Nickel-Catalyzed Proximal C-C Cleavage in Benzocyclobutenones with Insertion of 1,3-Diene: Origin of Selectivity and Role of Ligand.

  2016cites this paper
• Decarbonylative cross coupling of phthalimides with diorganozinc reagents—Efforts toward catalysis

  2016cites this paper
• Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system

  2016cites this paper
• Regiodivergent cyclobutanone cleavage: switching selectivity with different Lewis acids.

  2015cites this paper
• Cobalt(III)-Catalyzed Functionalization of Unstrained Carbon–Carbon Bonds through β-Carbon Cleavage of Alcohols

  2015cites this paper
• Nickel-Catalyzed Chemo-, Regio- and Diastereoselective Bond Formation through Proximal C-C Cleavage of Benzocyclobutenones.

  2015cites this paper
• Computational Study of Rh-Catalyzed Carboacylation of Olefins: Ligand-Promoted Rhodacycle Isomerization Enables Regioselective C-C Bond Functionalization of Benzocyclobutenones.

  2015cites this paper
• Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

  2015cites this paper
• Reversible C-C bond activation enables stereocontrol in Rh-catalyzed carbonylative cycloadditions of aminocyclopropanes.

  2015cites this paper
• Rh-catalyzed decarbonylation of conjugated ynones via carbon–alkyne bond activation: reaction scope and mechanistic exploration via DFT calculations

  2015cites this paper
• Catalytic intramolecular decarbonylative coupling of 3-aminocyclobutenones and alkenes: a unique approach to [3.1.0] bicycles.

  2015cites this paper
• Construction of Enantiopure Taxoid and Natural Product-like Scaffolds Using a C-C Bond Cleavage/Arylation Reaction.

  2015cites this paper
• Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy

  2015cites this paper
• Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals.

  2015cites this paper
• DFT Mechanistic Study of Functionalizations of ω-Ene-Cyclopropanes and Alkylidenecyclopropanes via Allylic C–H and C–C Bond Cleavage Facilitated by a Zirconocene Complex

  2015cites this paper
• Mechanistic Study on Ligand-Controlled Rh(I)-Catalyzed Coupling Reaction of Alkene-Benzocyclobutenone

  2015cites this paper
• Ceric ammonium nitrate (CAN) catalyzed modification of ketones via two C-C bond cleavages with the retention of the oxo-group.

  2014cites this paper
• Cobalt-catalyzed direct C–C bond formation between tetrahydrofuran and alkynes

  2014cites this paper
• Transition metal-catalyzed C-C bond activation of four-membered cyclic ketones.

  2014cites this paper
• Concise Synthesis of Functionalized Benzocyclobutenones.

  2014cites this paper
• Coupling of sterically hindered trisubstituted olefins and benzocyclobutenones by C-C activation: total synthesis and structural revision of cycloinumakiol.

  2014cites this paper
• Equilibration of the [2+2] Cycloaddition of Silyl Enol Ethers Catalyzed by Ethylaluminium Dichloride: Diastereoselectivity Switch in the Synthesis of Fused Cyclobutanes

  2014cites this paper
• A new approach for fused isoindolines via hexadehydro-Diels–Alder reaction (HDDA) by Fe(0) catalysis

  2014cites this paper