Site‐Selective C(sp3)‐H Alkenylation Using Decatungstate Anion as Photocatalyst

Site‐selective C(sp3)‐H alkenylation was achieved under photo‐irradiation in the presence of a catalytic amount of decatungstate anion, W10O324−. In this reaction, the radical addition/β‐scission sequence is successfully combined with photocatalytic C(sp3)‐H functionalization. The reaction using wea...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 364; no. 5; pp. 1039 - 1043
Main Authors Wang, Yi‐Ting, Shih, Yi‐Lun, Wu, Yen‐Ku, Ryu, Ilhyong
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2022
Wiley Subscription Services, Inc
Subjects
1,2-bis(sulfonyl)ethylene
Anions
benzenesulfonyl radical
Bonding strength
C(sp3)-H alkenylation
Chemistry
Chemistry, Applied
Chemistry, Organic
Cleavage
decatungstate anion
Hydrogen bonds
Photocatalysis
photocatalyst
Physical Sciences
Science & Technology
decatungstate anion
HYDROGEN-ATOM TRANSFER
VINYLATION
CYANATION
benzenesulfonyl radical
photocatalyst
ALKYNYLATION
FUNCTIONALIZATION
1
ALKENES
PHOTOINDUCED ALKYLATION
AMINO-ACIDS
C(sp)-H alkenylation
2-bis(sulfonyl)ethylene
ALKANES
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Summary:Site‐selective C(sp3)‐H alkenylation was achieved under photo‐irradiation in the presence of a catalytic amount of decatungstate anion, W10O324−. In this reaction, the radical addition/β‐scission sequence is successfully combined with photocatalytic C(sp3)‐H functionalization. The reaction using weaker C−H bonds such as those in THF revealed that the benzenesulfonyl radical itself underwent HAT directly from the C−H bond, and a decatungstate anion participated in a chain‐repairing step.
Bibliography:KAKEN
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202101374