Photochemical α-selective radical ring-opening reactions of 1,3-disubstituted acyl bicyclobutanes with alkyl halides: modular access to functionalized cyclobutenes

Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for synthesis of cyclobutanes, their application in the synthesis of cyclobutenes remains underdeveloped. Here, a novel visible light induced α-sel...

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Published inChemical science (Cambridge) Vol. 14; no. 45; pp. 136 - 1366
Main Authors Xiao, Yuanjiu, Xu, Tong-Tong, Zhou, Jin-Lan, Wu, Feng, Tang, Lei, Liu, Ruo-Yi, Wu, Wen-Biao, Feng, Jian-Jun
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 22.11.2023
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Halides
Photochemical reactions
Physical Sciences
Ring opening
Science & Technology
Substrates
Synthesis
INTERMOLECULAR 2+2 CYCLOADDITION
MERGING PHOTOREDOX
STRAIN-RELEASE
ENANTIOSELECTIVE SYNTHESIS
BUILDING-BLOCKS
CHEMISTRY
GENERATION
ADDITIONS
DERIVATIVES
PHOTOREDOX CATALYSIS
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Abstract Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for synthesis of cyclobutanes, their application in the synthesis of cyclobutenes remains underdeveloped. Here, a novel visible light induced α-selective radical ring-opening reaction of 1,3-disubstituted acyl bicyclobutanes with alkyl radical precursors for the synthesis of functionalized cyclobutenes is described. In particular, primary, secondary, and tertiary alkyl halides are all suitable substrates for this photocatalytic transformation, providing ready access to cyclobutenes with a single all-carbon quaternary center, or with two contiguous centers under mild reaction conditions. A protocol for synthesis of cyclobutenes through visible light initiated α-selective radical ring-opening of bicyclobutanes with alkyl radicals was achieved.
AbstractList Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for synthesis of cyclobutanes, their application in the synthesis of cyclobutenes remains underdeveloped. Here, a novel visible light induced α-selective radical ring-opening reaction of 1,3-disubstituted acyl bicyclobutanes with alkyl radical precursors for the synthesis of functionalized cyclobutenes is described. In particular, primary, secondary, and tertiary alkyl halides are all suitable substrates for this photocatalytic transformation, providing ready access to cyclobutenes with a single all-carbon quaternary center, or with two contiguous centers under mild reaction conditions. A protocol for synthesis of cyclobutenes through visible light initiated α-selective radical ring-opening of bicyclobutanes with alkyl radicals was achieved.
Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with beta-selectivity, have evolved as a powerful platform for synthesis of cyclobutanes, their application in the synthesis of cyclobutenes remains underdeveloped. Here, a novel visible light induced alpha-selective radical ring-opening reaction of 1,3-disubstituted acyl bicyclobutanes with alkyl radical precursors for the synthesis of functionalized cyclobutenes is described. In particular, primary, secondary, and tertiary alkyl halides are all suitable substrates for this photocatalytic transformation, providing ready access to cyclobutenes with a single all-carbon quaternary center, or with two contiguous centers under mild reaction conditions. A protocol for synthesis of cyclobutenes through visible light initiated alpha-selective radical ring-opening of bicyclobutanes with alkyl radicals was achieved.
Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for synthesis of cyclobutanes, their application in the synthesis of cyclobutenes remains underdeveloped. Here, a novel visible light induced α-selective radical ring-opening reaction of 1,3-disubstituted acyl bicyclobutanes with alkyl radical precursors for the synthesis of functionalized cyclobutenes is described. In particular, primary, secondary, and tertiary alkyl halides are all suitable substrates for this photocatalytic transformation, providing ready access to cyclobutenes with a single all-carbon quaternary center, or with two contiguous centers under mild reaction conditions.
Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for synthesis of cyclobutanes, their application in the synthesis of cyclobutenes remains underdeveloped. Here, a novel visible light induced α-selective radical ring-opening reaction of 1,3-disubstituted acyl bicyclobutanes with alkyl radical precursors for the synthesis of functionalized cyclobutenes is described. In particular, primary, secondary, and tertiary alkyl halides are all suitable substrates for this photocatalytic transformation, providing ready access to cyclobutenes with a single all-carbon quaternary center, or with two contiguous centers under mild reaction conditions.Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for synthesis of cyclobutanes, their application in the synthesis of cyclobutenes remains underdeveloped. Here, a novel visible light induced α-selective radical ring-opening reaction of 1,3-disubstituted acyl bicyclobutanes with alkyl radical precursors for the synthesis of functionalized cyclobutenes is described. In particular, primary, secondary, and tertiary alkyl halides are all suitable substrates for this photocatalytic transformation, providing ready access to cyclobutenes with a single all-carbon quaternary center, or with two contiguous centers under mild reaction conditions.
Author Xiao, Yuanjiu
Wu, Feng
Feng, Jian-Jun
Tang, Lei
Wu, Wen-Biao
Liu, Ruo-Yi
Xu, Tong-Tong
Zhou, Jin-Lan
AuthorAffiliation College of Chemistry and Chemical Engineering
State Key Laboratory of Chemo/Biosensing and Chemometrics
Advanced Catalytic Engineering Research Center of the Ministry of Education
Hunan University
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  name: Advanced Catalytic Engineering Research Center of the Ministry of Education
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  fullname: Xiao, Yuanjiu
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  givenname: Jin-Lan
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Keywords INTERMOLECULAR 2+2 CYCLOADDITION
MERGING PHOTOREDOX
STRAIN-RELEASE
ENANTIOSELECTIVE SYNTHESIS
BUILDING-BLOCKS
CHEMISTRY
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ADDITIONS
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Snippet Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with β-selectivity, have evolved as a powerful platform for...
Although ring-opening reactions of bicyclobutanes bearing electron-withdrawing groups, typically with beta-selectivity, have evolved as a powerful platform for...
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SubjectTerms Chemistry
Chemistry, Multidisciplinary
Halides
Photochemical reactions
Physical Sciences
Ring opening
Science & Technology
Substrates
Synthesis
Title Photochemical α-selective radical ring-opening reactions of 1,3-disubstituted acyl bicyclobutanes with alkyl halides: modular access to functionalized cyclobutenes
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