Multicomponent Annulative SO2 Insertion of Heteroatom‐Linked 1,7‐Diynes for Accessing Tricyclic Sulfones

A metal‐free radical multicomponent bicyclization of heteroatom‐linked 1,7‐diynes with aryl diazonium tetrafluoroborates and DABCO‐bis(sulfurdioxide) (DABSO) is reported, enabling annulative SO2 insertion access to produce two types of skeletally diverse tricyclic sulfones, namely, thieno[3,4‐c]quin...

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Published inAdvanced synthesis & catalysis Vol. 365; no. 10; pp. 1693 - 1698
Main Authors Wang, Lu, Shen, Yi‐Ting, Wang, Yu‐Xin, Wang, Hai‐Ying, Hao, Wen‐Juan, Jiang, Bo
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 23.05.2023
Wiley Subscription Services, Inc
Subjects
1,7-Diynes
Aromatic compounds
Chemistry
Chemistry, Applied
Chemistry, Organic
Double annulation
Free radicals
Insertion
Multicomponent reactions
Physical Sciences
Quinoline
Science & Technology
SO2 Insertion
Sulfones
Sulfur dioxide
Tricyclic sulfones
1
Double annulation
DESIGN
Multicomponent reactions
Tricyclic sulfones
SULFUR-DIOXIDE
SO2 Insertion
7-Diynes
Online AccessGet full text
ISSN1615-4150
1615-4169
DOI10.1002/adsc.202300272

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Abstract A metal‐free radical multicomponent bicyclization of heteroatom‐linked 1,7‐diynes with aryl diazonium tetrafluoroborates and DABCO‐bis(sulfurdioxide) (DABSO) is reported, enabling annulative SO2 insertion access to produce two types of skeletally diverse tricyclic sulfones, namely, thieno[3,4‐c]quinoline 2,2‐dioxides and thieno[3,4‐c]chromene 2,2‐dioxides, with moderate to good yields by simply tuning the linkers of the 1,7‐diynes. This protocol demonstrates remarkable compatibility regarding N‐ and O‐linked 1,7‐diynes with different substitution patterns and aryl diazonium tetrafluoroborates.
AbstractList A metal‐free radical multicomponent bicyclization of heteroatom‐linked 1,7‐diynes with aryl diazonium tetrafluoroborates and DABCO‐bis(sulfurdioxide) (DABSO) is reported, enabling annulative SO2 insertion access to produce two types of skeletally diverse tricyclic sulfones, namely, thieno[3,4‐c]quinoline 2,2‐dioxides and thieno[3,4‐c]chromene 2,2‐dioxides, with moderate to good yields by simply tuning the linkers of the 1,7‐diynes. This protocol demonstrates remarkable compatibility regarding N‐ and O‐linked 1,7‐diynes with different substitution patterns and aryl diazonium tetrafluoroborates.
Author Jiang, Bo
Shen, Yi‐Ting
Wang, Hai‐Ying
Hao, Wen‐Juan
Wang, Yu‐Xin
Wang, Lu
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Double annulation
DESIGN
Multicomponent reactions
Tricyclic sulfones
SULFUR-DIOXIDE
SO2 Insertion
7-Diynes
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Snippet A metal‐free radical multicomponent bicyclization of heteroatom‐linked 1,7‐diynes with aryl diazonium tetrafluoroborates and DABCO‐bis(sulfurdioxide) (DABSO)...
A metal-free radical multicomponent bicyclization of heteroatom-linked 1,7-diynes with aryl diazonium tetrafluoroborates and DABCO-bis(sulfurdioxide) (DABSO)...
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wiley
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SubjectTerms 1,7-Diynes
Aromatic compounds
Chemistry
Chemistry, Applied
Chemistry, Organic
Double annulation
Free radicals
Insertion
Multicomponent reactions
Physical Sciences
Quinoline
Science & Technology
SO2 Insertion
Sulfones
Sulfur dioxide
Tricyclic sulfones
Title Multicomponent Annulative SO2 Insertion of Heteroatom‐Linked 1,7‐Diynes for Accessing Tricyclic Sulfones
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadsc.202300272
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