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Borane-Catalyzed Stereoselective C–H Insertion, Cyclopropanation, and Ring-Opening Reactions

https://doi.org/10.1016/j.chempr.2020.06.035
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Outgoing claims: the papers this work cites, builds on, or argues with.

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Catalytic Functionalization of Indoles in a New Dimension
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Divergent Outcomes of Carbene Transfer Reactions from Dirhodium‐ and Copper‐Based Catalysts Separately or in Combination
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Pd/NbOPO4 Multifunctional Catalyst for the Direct Production of Liquid Alkanes from Aldol Adducts of Furans
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Enantioselective Palladium‐Catalyzed CH Functionalization of Indoles Using an Axially Chiral 2,2′‐Bipyridine Ligand
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Transition‐Metal Catalysis and Organocatalysis: Where Can Progress Be Expected?
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Group 6 Transition‐Metal/Boron Frustrated Lewis Pair Templates Activate N 2 and Allow its Facile Borylation and Silylation
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1,1‐Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP‐N2 Chemistry
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A Step Closer to Metal‐Free Dinitrogen Activation: A New Chapter in the Chemistry of Frustrated Lewis Pairs
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Synthesis of gem‐Difluoro Olefins through C−H Functionalization and β‐fluoride Elimination Reactions
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The Road Travelled: After Main‐Group Elements as Transition Metals
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Stoichiometric Photochemical Carbene Transfer by Bamford–Stevens Reaction
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Divergent Synthesis of Cyclopropane‐Containing Lead‐Like Compounds, Fragments and Building Blocks through a Cobalt Catalyzed Cyclopropanation of Phenyl Vinyl Sulfide
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Transition-metal catalyzed decomposition of aliphatic diazo compounds — New results and applications in organic synthesis
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Cyclopropane Derivatives and their Diverse Biological Activities
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Catalytic Asymmetric Dearomatization by Transition-Metal Catalysis: A Method for Transformations of Aromatic Compounds
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A review on recent developments of indole-containing antiviral agents
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Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion
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Transition Metal Vinylidene- and Allenylidene-Mediated Catalysis in Organic Synthesis
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Boron-Catalyzed Azide Insertion of α-Aryl α-Diazoesters
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Mechanistic Insights into the Chemo- and Regio-Selective B(C6F5)3 Catalyzed C–H Functionalization of Phenols with Diazoesters
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Toxicity of Metal Compounds: Knowledge and Myths
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Gold-Catalyzed Controllable C2-Functionalization of Benzofurans with Aryl Diazoesters
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Palladium-Catalyzed C–H Arylation of Indoles at the C7 Position
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Testing the Push–Pull Hypothesis: Lewis Acid Augmented N2 Activation at Iron
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CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence
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Main-group elements as transition metals
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C–H bond activation enables the rapid construction and late-stage diversification of functional molecules
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Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates
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Iodine-catalyzed diazo activation to access radical reactivity
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Synthesis of natural products containing the pyrrolic ring
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Bulky derivatives of boranes, boronic acids and boronate estersvia reaction with diazomethanes
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CuO/SiO2 as a simple, effective and recoverable catalyst for alkylation of indole derivatives with diazo compounds
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An enantioselective three-component reaction of diazoacetates with indoles and enals by iridium/iminium co-catalysis
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Sulphanilic acid as a recyclable bifunctional organocatalyst in the selective conversion of lignocellulosic biomass to 5-HMF
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Push and pull: the potential role of boron in N 2 activation
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Blue light-promoted photolysis of aryldiazoacetates
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Bis(imino)pyridine iron complexes for catalytic carbene transfer reactions
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Rhodium-catalyzed, P-directed selective C7 arylation of indoles
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Metal-free catalytic C-H bond activation and borylation of heteroarenes
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The broadening reach of frustrated Lewis pair chemistry
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Nitrogen fixation and reduction at boron
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Frontiers in molecular p-block chemistry: From structure to reactivity
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The reductive coupling of dinitrogen
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Use of furans in synthesis of bioactive compounds

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Cyclopropanation of Unactivated Alkenes with Non-Stabilized Carbenes
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Triarylboranes in the Activation of Azo‐Containing Compounds
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Recent Advances in Boron‐Mediated CH Functionalization
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Boron‐Catalyzed Dehydrative Friedel‐Crafts Alkylation of Arenes Using β‐Hydroxyl Ketone as MVK Precursor
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Borane Catalyzed Selective Diazo Cross‐Coupling Towards Pyrazoles
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Tris(pentafluorophenyl)borane‐Catalyzed Oxygen Insertion Reaction of α‐Diazoesters (α‐Diazoamides) with Dimethyl Sulfoxide
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Borane‐Catalyzed, HFIP‐Assisted Carbene Insertion into Internal Alkenyl C−H Bonds under Metal‐Free Conditions
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Brønsted acid‐catalyzed Reactions of Unprotected N‐heterocycles with Aryl/Aryl Diazoalkanes
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Facile and Efficient SynthesisofFluorene and Indenoarene Carboxylates from Biaryldiazoacetates via BlueLight‐promoted Intramolecular CarbeneC−H Insertion
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Tris(pentafluorphenyl)boran‐katalysierte Erzeugung von Carbenium‐Ionen und autokatalytische Pyrazol‐Synthese – eine theoretische und experimentelle Studie
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Rhodium(I) Carbene‐Promoted Enantioselective C−H Functionalization of Simple Unprotected Indoles, Pyrroles and Heteroanalogues: New Mechanistic Insights
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Aromative Dephosphinidenation of a Bisphosphirane‐Fused Anthracene toward E−H (E=H, Si, N and P) Bond Activation
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“Boron Ylide” Enables Stereoselective Construction of gem ‐Diborylcyclopropanes
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Modular Synchronous Synthesis of Amides and α‐Ketoamides Realized by Matching Electrolysis‐Paired Tandems
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Tris(pentafluorophenyl)borane‐Catalyzed Carbenium Ion Generation and Autocatalytic Pyrazole Synthesis—A Computational and Experimental Study
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Rhodium(I) Carbene‐Promoted Enantioselective C−H Functionalization of Simple Unprotected Indoles, Pyrroles and Heteroanalogues: New Mechanistic Insights
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Aromative Dephosphinidenation of a Bisphosphirane‐Fused Anthracene toward E−H (E=H, Si, N and P) Bond Activation
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“Boron Ylide” Enables Stereoselective Construction of gem ‐Diborylcyclopropanes
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Modular Synchronous Synthesis of Amides and α‐Ketoamides Realized by Matching Electrolysis‐Paired Tandems
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Solvent‐free, B(C6F5)3‐Catalyzed S−H Insertion of Thiophenols and Thiols with α‐Diazoesters
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Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale
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B(C6F5)3‐Catalyzed [2+3]‐Cyclative o,m‐diC‐H Functionalization of Phenols
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Acid‐Catalyzed Carbene Transfer from Diazo Compounds: Carbocation versus Carbene as Key Intermediate
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Dual Catalysis Involving Organoboron Compounds
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B(C 6 F 5 ) 3 ‐Catalyzed 1,4‐Allylation of Azadienes with Allyltrimethylsilanes
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Strategies Employing Transition‐Metal Free Conditions for C−C Bond Formation in Indoles
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Catalyst Free Chemoselective Carbene Insertion Into COO─H Bond Over ─OH of Salicylic Acid
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Recent advances in boron chemistry
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Directed Aryl C–H Oxidations With Main Group Metals
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Aldehydes: α,β-Unsaturated Aldehydes
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Recent applications of fluorinated arylborane derivatives
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Cyclopropanation of unactivated alkenes with non-stabilized iron carbenes
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DFT quest for mechanism and stereoselectivity in B(C6F5)3-catalyzed cyclopropanation of alkenes with aryldiazoacetates
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Phenylpyridine-Based Borenium Salts as Lewis Acid Catalysts for Homocoupling of Diaryldiazomethanes
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Reaction of Diazo Compounds with Borenium Ions: C–H Bond Activation/Annulation vs 1,1-Carboboration
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Pathway to Construct α-Acyloxy Esters by B(C6F5)3-Catalyzed O–H Insertion of Carboxylic Acids with Sulfoxonium Ylides
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Accessing Highly Substituted Indoles via B(C6F5)3-Catalyzed Secondary Alkyl Group Transfer
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B(C6F5)3·H2O-Catalyzed N–H and C–H Functionalization of Aromatic Amines with Sulfoxonium Ylides under Metal-Free Conditions
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DFT Insights into the Mechanistic Switch from Carbene to Carbocation in B(C 6 F 5 ) 3 -Catalyzed Coupling of Diazooxindoles and Difluoroenoxysilanes in HFIP
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Copper-Catalyzed Intermolecular Cyclopropanation of Benzofurans and Indoles
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Borane-Catalyzed Divergent Hydrogenative and Silylative Reduction of Quinolinium Salts
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B(C6F5)3-Catalyzed β-Functionalization of Pyrrolidines Using Isatins via Borrowing Hydrogen: Divergent Access to Substituted Pyrrolidines and Pyrroles
inferred← citeshttps://doi.org/10.1021/acs.orglett.0c03653openalex-snapshot
Site-Selective Functionalization of 7-Azaindoles via Carbene Transfer and Isolation of N-Aromatic Zwitterions
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Tropylium-Catalyzed O–H Insertion Reactions of Diazoalkanes with Carboxylic Acids
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B(C6F5)3-Catalyzed Sequential Additions of Terminal Alkynes to para-Substituted Phenols: Selective Construction of Congested Phenol-Substituted Quaternary Carbons
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Borane-Catalyzed Carbazolation Reactions of Aryldiazoacetates
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Enantioselective Indole Insertion Reactions of α-Carbonyl Sulfoxonium Ylides
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Catalytic Transformations of 2-Pyridones by Rhodium-Mediated Carbene Transfer
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B(C6F5)3-Catalyzed Diastereoselective and Divergent Reactions of Vinyldiazo Esters with Nitrones: Synthesis of Highly Functionalized Diazo Compounds
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Borane-Catalyzed Coupling of Diazooxindoles and Difluoroenoxysilanes to Tetrasubstituted Monofluoroalkenes
inferred← citeshttps://doi.org/10.1021/acs.orglett.5c00712openalex-snapshot
Chiral Phosphoric Acid Catalyzed Asymmetric Mannich Reaction of 2-Aryl-3H-indol-3-ones with α-H Diazoacetates
inferred← citeshttps://doi.org/10.1021/acs.orglett.5c03085openalex-snapshot
Stereoselective Synthesis of π-Enriched Conjugated Dienynals via Photochemical Alkynyl Carbene Insertion into Furans
inferred← citeshttps://doi.org/10.1021/acs.orglett.5c04254openalex-snapshot
Access to Conjugated Dienes and Cyclic Allenes via a Diazo-Dithiane Rearrangement Cascade
inferred← citeshttps://doi.org/10.1021/acs.orglett.5c04464openalex-snapshot
Diastereoselective Cascade Annulation of Distal Formyl Enones and Sulfur Ylides toward Cyclopropane-Fused Cycloalkanes
inferred← citeshttps://doi.org/10.1021/acscatal.0c03218openalex-snapshot
Tris(pentafluorophenyl)borane-Catalyzed Cyclopropanation of Styrenes with Aryldiazoacetates
inferred← citeshttps://doi.org/10.1021/acscatal.1c01051openalex-snapshot
Catalyst-Directed Divergent Catalytic Approaches to Expand Structural and Functional Scaffold Diversity via Metallo-Enolcarbene Intermediates
inferred← citeshttps://doi.org/10.1021/acscatal.1c04746openalex-snapshot
Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors
inferred← citeshttps://doi.org/10.1021/acscatal.2c04504openalex-snapshot
Mechanistic Investigation on Dearomative Spirocyclization of Arenes with α-Diazoamide under Boron Catalysis
inferred← citeshttps://doi.org/10.1021/acscatal.2c04605openalex-snapshot
Piers’ Borane-Catalyzed Dimerization of Arylallenes via Transborylation: A Synthetic and Mechanistic Study
inferred← citeshttps://doi.org/10.1021/acscatal.4c03368openalex-snapshot
Comparison of the Efficiency of B–O and B–C Bond Formation Pathways in Borane-Catalyzed Carbene Transfer Reactions Using α-Diazocarbonyl Precursors: A Combined Density Functional Theory and Machine Learning Study
inferred← citeshttps://doi.org/10.1021/acsomega.2c00200openalex-snapshot
DFT Mechanistic Study of the Cyclopropanation of Styrene and Aryldiazodiacetate Catalyzed by Tris(pentafluorophenyl)borane
inferred← citeshttps://doi.org/10.1021/acsomega.3c07367openalex-snapshot
Kinetics of N 2 Release from Diazo Compounds: A Combined Machine Learning-Density Functional Theory Study
inferred← citeshttps://doi.org/10.1021/jacs.3c05278openalex-snapshot
Borane-Catalyzed C–F Bond Functionalization of gem-Difluorocyclopropenes Enables the Synthesis of Orphaned Cyclopropanes
inferred← citeshttps://doi.org/10.1021/jacs.5c03146openalex-snapshot
Empowering Diastereoselective Cyclopropanation of Unactivated Alkenes with Sulfur Ylides through Nucleopalladation
inferred← citeshttps://doi.org/10.1021/jacs.5c17932openalex-snapshot
Thiol-Free Sulfenylation Redefined: A Single-Atom Transfer Pathway to Symmetrical Di(hetero)arylthioethers via B(C 6 F 5 ) 3 Catalysis
inferred← citeshttps://doi.org/10.1039/d0cy01339kopenalex-snapshot
Triarylborane catalysed N -alkylation of amines with aryl esters
inferred← citeshttps://doi.org/10.1039/d0ob02478copenalex-snapshot
Tris(pentafluorophenyl)borane catalyzed C–C and C–heteroatom bond formation
inferred← citeshttps://doi.org/10.1039/d1cc01026copenalex-snapshot
N -Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C–H alkylation of indoles
inferred← citeshttps://doi.org/10.1039/d1cc01856fopenalex-snapshot
Borane catalysed cyclopropenation of arylacetylenes
inferred← citeshttps://doi.org/10.1039/d1cc03048eopenalex-snapshot
B(C 6 F 5 ) 3 -Catalyzed site-selective N 1 -alkylation of benzotriazoles with diazoalkanes
inferred← citeshttps://doi.org/10.1039/d1cs00895aopenalex-snapshot
Recent advances in transition-metal-catalyzed carbene insertion to C–H bonds
inferred← citeshttps://doi.org/10.1039/d1gc00191dopenalex-snapshot
Dehydrative allylation of P–H species under metal-free conditions
inferred← citeshttps://doi.org/10.1039/d1ob00520kopenalex-snapshot
The synthesis, properties, and reactivity of Lewis acidic aminoboranes
inferred← citeshttps://doi.org/10.1039/d1ob01035bopenalex-snapshot
B(C 6 F 5 ) 3 -catalyzed O–H insertion reactions of diazoalkanes with phosphinic acids
inferred← citeshttps://doi.org/10.1039/d1qo01184gopenalex-snapshot
Regiospecific and site-selective C–H allylation of phenols with vinyldiazo compounds catalyzed by In( iii )
inferred← citeshttps://doi.org/10.1039/d2cc00099gopenalex-snapshot
Silver-catalyzed cyclopropanation of alkenes with alkynyl N -nosylhydrazones leading to alkynyl cyclopropanes
inferred← citeshttps://doi.org/10.1039/d2cc06744gopenalex-snapshot
B(C 6 F 5 ) 3 -catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes
inferred← citeshttps://doi.org/10.1039/d2nj05584hopenalex-snapshot
Cobalt-catalyzed esterification-peroxidation of α-diazoesters: access to α-acyloxy esters
inferred← citeshttps://doi.org/10.1039/d2ob00447jopenalex-snapshot
Borane-catalyzed arylation of aryldiazoacetates with N , N -dialkylanilines
inferred← citeshttps://doi.org/10.1039/d2ob01048hopenalex-snapshot
Catalyst-dependent chemoselective insertion of diazoalkanes into the N–H/C–H/O–H/C–O bonds of 2-hydroxybenzothiazoles
inferred← citeshttps://doi.org/10.1039/d2ob01273aopenalex-snapshot
Electrochemical S–H and O–H insertion reactions from thiols or salicylic acids with diazo esters
inferred← citeshttps://doi.org/10.1039/d2qo00552bopenalex-snapshot
Borane-catalyzed dehydrogenative C–C bond formation of indoles with N -tosylhydrazones: an experimental and computational study
inferred← citeshttps://doi.org/10.1039/d2ra05739eopenalex-snapshot
B(C 6 F 5 ) 3 -catalyzed oxidation of α-diazoesters using DMF and molecular oxygen as oxygen sources
inferred← citeshttps://doi.org/10.1039/d2sc00203eopenalex-snapshot
Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes
inferred← citeshttps://doi.org/10.1039/d3dt00745fopenalex-snapshot
B(3,4,5-F 3 H 2 C 6 ) 3 Lewis acid-catalysed C3-allylation of indoles
inferred← citeshttps://doi.org/10.1039/d3ob00894kopenalex-snapshot
Aryl boronic acid-controlled divergent ring-contraction and ring-opening/isomerization reaction of tert -cyclobutanols enabled by nickel catalysis
inferred← citeshttps://doi.org/10.1039/d3ob01548copenalex-snapshot
Borane catalyzed transesterification of tert -butyl esters using α-aryl α-diazoesters
inferred← citeshttps://doi.org/10.1039/d3qo00054kopenalex-snapshot
B(C 6 F 5 ) 3 -catalyzed Wolff rearrangement/[2 + 2] and [4 + 2] cascade cyclization of α-diazoketones with imines
inferred← citeshttps://doi.org/10.1039/d3qo01693eopenalex-snapshot
Synthesis of cyclic silyl enol ethers from α-Aryl-α-diazoketones: new building blocks for preparation of indanones and α,β-unsaturated ketones
inferred← citeshttps://doi.org/10.1039/d4qo00998copenalex-snapshot
Dirhodium( ii )-catalyzed regio- and stereoselective cycloisomerization towards 6,5,3-tricyclic skeletons containing vicinal all-carbon quaternary stereocenters
inferred← citeshttps://doi.org/10.1039/d5cc03734dopenalex-snapshot
Harnessing the power of α-diazo compounds: emerging strategies and expanding applications
inferred← citeshttps://doi.org/10.1039/d5ra06138eopenalex-snapshot
NaHMDS/B(C 6 F 5 ) 3 -promoted diastereoselective Friedel–Crafts alkylation of indoles/pyrroles with N-tert -butanesulfinylimines: towards the asymmetric synthesis of bisindole alkaloid Calcicamide B
inferred← citeshttps://doi.org/10.1055/a-2118-3046openalex-snapshot
Activation of Diazo Compounds by Fluorinated Triarylborane Catalysts
inferred← citeshttps://doi.org/10.3390/catal12010005openalex-snapshot
Boron-Based Lewis Acid Catalysis: Challenges and Perspectives
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