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Photoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals

https://doi.org/10.1021/acs.orglett.0c02513

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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1002/anie.201209833openalex-snapshot

CC Fragmentation: Origins and Recent Applications

inferredcites →https://doi.org/10.1002/anie.201510014openalex-snapshot

Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp 3 )−H Functionalization under Mild Reaction Conditions

inferredcites →https://doi.org/10.1002/anie.201607305openalex-snapshot

Catalytic Asymmetric C−H Functionalization under Photoredox Conditions by Radical Translocation and Stereocontrolled Alkene Addition

inferredcites →https://doi.org/10.1002/anie.201609035openalex-snapshot

Photocatalytic C−C Bond Cleavage and Amination of Cycloalkanols by Cerium(III) Chloride Complex

inferredcites →https://doi.org/10.1002/anie.201707171openalex-snapshot

Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal‐Free C(sp 3 )–C(sp 3 ) Cleavage and Allylation/Alkenylation

inferredcites →https://doi.org/10.1002/anie.201710618openalex-snapshot

A Visible‐Light‐Driven Iminyl Radical‐Mediated C−C Single Bond Cleavage/Radical Addition Cascade of Oxime Esters

inferredcites →https://doi.org/10.1002/anie.201710790openalex-snapshot

Photoinduced Remote Functionalisations by Iminyl Radical Promoted C−C and C−H Bond Cleavage Cascades

inferredcites →https://doi.org/10.1002/anie.201809608openalex-snapshot

Selective C−N Borylation of Alkyl Amines Promoted by Lewis Base

inferredcites →https://doi.org/10.1002/anie.201904028openalex-snapshot

Deoxygenative Borylation of Secondary and Tertiary Alcohols

inferredcites →https://doi.org/10.1002/anie.201905218openalex-snapshot

Radical‐Promoted C−C Bond Cleavage: A Deconstructive Approach for Selective Functionalization

inferredcites →https://doi.org/10.1002/anie.201910051openalex-snapshot

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

inferredcites →https://doi.org/10.1002/chem.201804246openalex-snapshot

Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

inferredcites →https://doi.org/10.1002/chem.201901762openalex-snapshot

Visible‐Light‐Promoted Ring‐Opening Alkynylation, Alkenylation, and Allylation of Cyclic Hemiacetals through β‐Scission of Alkoxy Radicals

inferredcites →https://doi.org/10.1002/cjoc.201800206openalex-snapshot

Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters

inferredcites →https://doi.org/10.1002/cjoc.201800455openalex-snapshot

Recent Advances in Radical‐Mediated C—C Bond Fragmentation of Non‐Strained Molecules

inferredcites →https://doi.org/10.1002/cjoc.201800500openalex-snapshot

Free Radical Pathway Cleavage of C—O Bonds for the Synthesis of Alkylboron Compounds

inferredcites →https://doi.org/10.1002/ejoc.200400131openalex-snapshot

B‐Alkylcatecholborane‐Mediated Radical Reactions

inferredcites →https://doi.org/10.1016/j.chempr.2019.11.009openalex-snapshot

Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis

inferredcites →https://doi.org/10.1016/j.tetlet.2018.04.060openalex-snapshot

Photocatalytic alkoxy radical-mediated transformations

inferredcites →https://doi.org/10.1016/s0040-4039(99)01482-3openalex-snapshot

Synthesis of alditols by reductive radical fragmentation of N-phthalimido glycosides. Preparation of chiral synthetic intermediates

inferredcites →https://doi.org/10.1021/acs.chemrev.0c00030openalex-snapshot

Visible Light-Driven Radical-Mediated C–C Bond Cleavage/Functionalization in Organic Synthesis

inferredcites →https://doi.org/10.1021/acs.chemrev.6b00599openalex-snapshot

Recent Methodologies That Exploit C–C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes

inferredcites →https://doi.org/10.1021/acs.joc.8b01225openalex-snapshot

Visible-Light-Mediated Ring-Opening Strategy for the Regiospecific Allylation/Formylation of Cycloalkanols

inferredcites →https://doi.org/10.1021/acs.orglett.7b01181openalex-snapshot

Decarboxylative Borylation of Aliphatic Esters under Visible-Light Photoredox Conditions

inferredcites →https://doi.org/10.1021/acs.orglett.9b00874openalex-snapshot

Synthesis of Functionalized Organoboron/Silicon Compounds by Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Diboron/Silylborane Reagents

inferredcites →https://doi.org/10.1021/acscatal.8b02928openalex-snapshot

Cu-Catalyzed Decarboxylative Borylation

inferredcites →https://doi.org/10.1021/jacs.0c01416openalex-snapshot

Synthetic Methods Driven by the Photoactivity of Electron Donor–Acceptor Complexes

inferredcites →https://doi.org/10.1021/jacs.0c03813openalex-snapshot

Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones

inferredcites →https://doi.org/10.1021/jacs.5b13066openalex-snapshot

Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp 3 )–C(sp 3 ) Bond Cleavage and Functionalizations

inferredcites →https://doi.org/10.1021/jacs.6b06517openalex-snapshot

Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O–H Bonds

inferredcites →https://doi.org/10.1021/jacs.8b03333openalex-snapshot

Transition Metal-Free 1,2-Carboboration of Unactivated Alkenes

inferredcites →https://doi.org/10.1021/jacs.8b07103openalex-snapshot

Photoinduced Deaminative Borylation of Alkylamines

inferredcites →https://doi.org/10.1021/jacs.8b08781openalex-snapshot

Cerium-Catalyzed Formal Cycloaddition of Cycloalkanols with Alkenes through Dual Photoexcitation

inferredcites →https://doi.org/10.1021/jacs.8b12552openalex-snapshot

A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C–C Bond Cleavage Reactions

inferredcites →https://doi.org/10.1021/jo502499aopenalex-snapshot

Strategies to Control Alkoxy Radical-Initiated Relay Cyclizations for the Synthesis of Oxygenated Tetrahydrofuran Motifs

inferredcites →https://doi.org/10.1021/ol202740wopenalex-snapshot

Photoinduced Electron-Transfer-Promoted Redox Fragmentation of N -Alkoxyphthalimides

inferredcites →https://doi.org/10.1021/ol802142kopenalex-snapshot

Chemoselective Oxygen-Centered Radical Cyclizations onto Silyl Enol Ethers

inferredcites →https://doi.org/10.1021/ol900481eopenalex-snapshot

Construction of Carbo- and Heterocycles Using Radical Relay Cyclizations Initiated by Alkoxy Radicals

inferredcites →https://doi.org/10.1038/s41586-018-0700-3openalex-snapshot

Deconstructive diversification of cyclic amines

inferredcites →https://doi.org/10.1039/c4qo00053fopenalex-snapshot

Direct activation of relatively unstrained carbon–carbon bonds in homogeneous systems

inferredcites →https://doi.org/10.1039/c7cc01254copenalex-snapshot

Stereospecific functionalizations and transformations of secondary and tertiary boronic esters

inferredcites →https://doi.org/10.1039/c8cc02642dopenalex-snapshot

Visible-light-induced alkoxyl radical generation for inert chemical bond cleavage/functionalization

inferredcites →https://doi.org/10.1039/c8cs00386fopenalex-snapshot

Cleavage of carbon–carbon bonds by radical reactions

inferredcites →https://doi.org/10.1039/c8ob02987copenalex-snapshot

A photocatalytic sp 3 C–S, C–Se and C–B bond formation through C–C bond cleavage of cycloketone oxime esters

inferredcites →https://doi.org/10.1039/c8qo00747kopenalex-snapshot

Photoinduced fragmentation-rearrangement sequence of cycloketoxime esters

inferredcites →https://doi.org/10.1039/c8sc01763hopenalex-snapshot

Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C–C bond scission

inferredcites →https://doi.org/10.1039/c8sc03315copenalex-snapshot

Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters

inferredcites →https://doi.org/10.1039/c9qo00472fopenalex-snapshot

Copper-catalyzed borylation of cycloalkylsilyl peroxides via radical C–C bond cleavage

inferredcites →https://doi.org/10.1039/c9sc02616aopenalex-snapshot

A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades

inferredcites →https://doi.org/10.1055/s-1998-1711openalex-snapshot

Facile Generation of Alkoxy Radicals from N-Alkoxyphthalimides

inferredcites →https://doi.org/10.1126/science.aam7355openalex-snapshot

Decarboxylative borylation

inferredcites →https://doi.org/10.1126/science.aan3679openalex-snapshot

Photoinduced decarboxylative borylation of carboxylic acids

inferredcites →https://doi.org/10.1246/cl.170834openalex-snapshot

β-Scission of Alkoxy Radicals in Synthetic Transformations

What points at this work

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

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Generation and Radical-Radical Cross-Coupling of Alkenyloxy Radical: Ester and Ketone Synthesis

inferred← citeshttps://doi.org/10.1002/047084289x.rn00591.pub2openalex-snapshot

Bis(catecholatodiboron)

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Radical Reactions

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Catalyst‐Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor‐Acceptor Complex Photoactivation

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Photocatalyst‐Free Wavelength‐Dependent Sequential Ring Transformations of Pyrazolo[1,2‐ a ]pyrazolones

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Photoinduced Electron Donor–Acceptor Complex Strategy for Forging CS Bond via β ‐Fragmentation of Alkoxy Radicals

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Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

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Alkoxy Radical Induced Transformations from N‐Alkoxyphthalimides Under the Photoredox Catalysis

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Nucleophilic and Radical Heptafluoroisopropoxylation with Redox‐Active Reagents

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Radical Borylation of Alkyl Bromides by Photoinduced Halogen‐Atom Transfer

inferred← citeshttps://doi.org/10.1002/anie.202109572openalex-snapshot

Nucleophilic and Radical Heptafluoroisopropoxylation with Redox‐Active Reagents

inferred← citeshttps://doi.org/10.1002/anie.202510162openalex-snapshot

Radical Borylation of Alkyl Bromides by Photoinduced Halogen‐Atom Transfer

inferred← citeshttps://doi.org/10.1002/chem.202004692openalex-snapshot

(o‐Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors

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A Metal‐Free and Operationally Simple Radical Trifluoromethylative Borylation of Unactivated Alkenes

inferred← citeshttps://doi.org/10.1002/cjoc.202400694openalex-snapshot

Recent Advances in Methodologies for Radical‐Mechanistic Borylation †

inferred← citeshttps://doi.org/10.1002/ejoc.202200330openalex-snapshot

Radical Deoxyfunctionalisation Strategies**

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Transition‐Metal‐Free Radical Borylation Reactions

inferred← citeshttps://doi.org/10.1002/ejoc.202300085openalex-snapshot

Concise Synthesis, Conformational Study, and Aroma Properties of Carba‐Homologues of Helvetolide and Serenolide

inferred← citeshttps://doi.org/10.1002/open.202300285openalex-snapshot

A Computational Study of Photoinduced Borylation for Selected Boron Sources

inferred← citeshttps://doi.org/10.1002/tcr.202400161openalex-snapshot

Organometallic Photocatalyst‐Promoted Synthesis and Modification of Carbohydrates under Photoirradiation

inferred← citeshttps://doi.org/10.1016/b978-0-443-31482-7.00127-2openalex-snapshot

Alkylboron and -Silicon Compounds

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Photocatalyst-free light-promoted carbohydrate synthesis and modification

inferred← citeshttps://doi.org/10.1016/j.checat.2021.03.014openalex-snapshot

Alkoxyl-radical-mediated synthesis of functionalized allyl tert-(hetero)cyclobutanols and their ring-opening and ring-expansion functionalizations

inferred← citeshttps://doi.org/10.1016/j.checat.2022.07.002openalex-snapshot

Photoinduced ring-opening olefination of cycloalkanols and access to tunable cycloenones

inferred← citeshttps://doi.org/10.1016/j.chempr.2022.07.022openalex-snapshot

General and selective metal-free radical α-C–H borylation of aliphatic amines

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Highly efficient electrogeneration of oxygen centered radicals from N-alkoxyphthalimides employing rapid alternating polarity (RAP) electrolysis. Transferring the photoredox catalytic conditions to organic electrosynthesis

inferred← citeshttps://doi.org/10.1016/j.tet.2020.131867openalex-snapshot

Photo-induced radical borylation of hemiacetals via C–C bond cleavage

inferred← citeshttps://doi.org/10.1021/acs.chemrev.1c00256openalex-snapshot

Alkoxy Radicals See the Light: New Paradigms of Photochemical Synthesis

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Metal- and Photocatalyst-Free, Visible-Light-Initiated C3 α-Aminomethylation of Quinoxalin-2(1 H )-ones via Electron Donor–Acceptor Complexes

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N-Alkoxyphthalimides as Nitrogen Electrophiles to Construct C–N Bonds via Reductive Cross-Coupling

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Photoinduced Deconstructive Alkylation Approach Enabled by Oxy-Radicals from Alcohols

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Unified Divergent Total Syntheses of Illudalane Sesquiterpenes from Granulolactone via a One-Pot Diels–Alder/Oxidative Aromatization

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Visible Light-Enabled Oxo-Alkylation of Styrenes with Aliphatic Alcohol Derivatives for the Synthesis of α-Alkyl Ketones

inferred← citeshttps://doi.org/10.1021/acs.orglett.1c01080openalex-snapshot

Light-Mediated Sulfur–Boron Exchange

inferred← citeshttps://doi.org/10.1021/acs.orglett.3c02038openalex-snapshot

Photoinduced Borylation of the Inert C(sp3)–O Bond of Alkyl Heteroaryl Ethers

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Visible-Light-Driven Decarboxylative Borylation: Rapid Access to α- and β-Amino-boronamides

inferred← citeshttps://doi.org/10.1021/acs.orglett.4c00627openalex-snapshot

Generation and Radical–Radical Cross-Coupling of Alkenyloxy Radical

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Zn-Mediated Fragmentation of N-Alkoxyphthalimides Enabling the Synthesis of gem-Difluoroalkenes

inferred← citeshttps://doi.org/10.1021/acs.orglett.6c01570openalex-snapshot

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Programmable Synthesis of 1, n -Dicarbonyls Enabled by Photoinduced β-Fragmentation of Alkoxy Radicals from Cycloalkanols

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Alcohols as Alkyl Synthons Enabled by Photoredox-Catalyzed Deoxygenative Activation

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Persistent Boryl Radicals as Highly Reducing Photoredox Catalysts for Debrominative Borylations

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Metal-free, photoinduced remote C(sp 3 )–H borylation

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Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry

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Photoinduced alkylation of pyrazolones via β-scission of unstrained aliphatic alcohol derivatives

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