Alkynyl Sulfonium Salts Can Be Employed as Chalcogen‐Bonding Catalysts and Generate Alkynyl Radicals under Blue‐Light Irradiation

Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well‐developed selenium‐ and tellurium‐based salt catalysts, the ChB catalysis of sulfonium salts is still unknown. Here, we report a new type of alkynyl‐sulfonium salt ChB catalysis for various...

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Published inAngewandte Chemie International Edition Vol. 61; no. 16; pp. e202116071 - n/a
Main Authors Lu, Yu, Liu, Qiang, Wang, Zhi‐Xiang, Chen, Xiang‐Yu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 11.04.2022
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkynyl Radical
Alkynyl-Sulfonium Salt
Bonding
Bromination
Catalysis
Catalysts
Chalcogen Bonding
Chalcogen bonds
Chalcogenoacetylenes
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Dimerization
Irradiation
Light irradiation
Michael reaction
Physical Sciences
Radiation
Radicals
Salts
Science & Technology
Selenium
Sulfonium salts
Tellurium
SULFOXIDES
Alkynyl-Sulfonium Salt
TELLURIDES
Chalcogen Bonding
SELENIDES
Alkynyl Radical
Catalysis
C-H FUNCTIONALIZATION
Chalcogenoacetylenes
EFFICIENT
Online AccessGet full text

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Abstract Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well‐developed selenium‐ and tellurium‐based salt catalysts, the ChB catalysis of sulfonium salts is still unknown. Here, we report a new type of alkynyl‐sulfonium salt ChB catalysis for various ionic transformations, including transfer hydrogenation, bromination, bromolactonization, dimerization of 1,1‐diphenylethylene, nitro‐Michael addition reaction and Ritter reaction. More importantly, the photocapability of ChB was first demonstrated to generate alkynyl radicals for the synthesis of a variety of chalcogenoacetylenes. Mechanistic studies shed light on the mechanism of the photoinduced reactions and confirmed the involvement of alkynyl radicals which are difficult to generate otherwise. Alkynyl sulfonium salts were employed as chalcogen bonding (ChB) catalysts for the first time. They display superior capability in the generation of alkynyl radicals under blue‐light irradiation.
AbstractList Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well‐developed selenium‐ and tellurium‐based salt catalysts, the ChB catalysis of sulfonium salts is still unknown. Here, we report a new type of alkynyl‐sulfonium salt ChB catalysis for various ionic transformations, including transfer hydrogenation, bromination, bromolactonization, dimerization of 1,1‐diphenylethylene, nitro‐Michael addition reaction and Ritter reaction. More importantly, the photocapability of ChB was first demonstrated to generate alkynyl radicals for the synthesis of a variety of chalcogenoacetylenes. Mechanistic studies shed light on the mechanism of the photoinduced reactions and confirmed the involvement of alkynyl radicals which are difficult to generate otherwise.
Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well-developed selenium- and tellurium-based salt catalysts, the ChB catalysis of sulfonium salts is still unknown. Here, we report a new type of alkynyl-sulfonium salt ChB catalysis for various ionic transformations, including transfer hydrogenation, bromination, bromolactonization, dimerization of 1,1-diphenylethylene, nitro-Michael addition reaction and Ritter reaction. More importantly, the photocapability of ChB was first demonstrated to generate alkynyl radicals for the synthesis of a variety of chalcogenoacetylenes. Mechanistic studies shed light on the mechanism of the photoinduced reactions and confirmed the involvement of alkynyl radicals which are difficult to generate otherwise.Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well-developed selenium- and tellurium-based salt catalysts, the ChB catalysis of sulfonium salts is still unknown. Here, we report a new type of alkynyl-sulfonium salt ChB catalysis for various ionic transformations, including transfer hydrogenation, bromination, bromolactonization, dimerization of 1,1-diphenylethylene, nitro-Michael addition reaction and Ritter reaction. More importantly, the photocapability of ChB was first demonstrated to generate alkynyl radicals for the synthesis of a variety of chalcogenoacetylenes. Mechanistic studies shed light on the mechanism of the photoinduced reactions and confirmed the involvement of alkynyl radicals which are difficult to generate otherwise.
Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well‐developed selenium‐ and tellurium‐based salt catalysts, the ChB catalysis of sulfonium salts is still unknown. Here, we report a new type of alkynyl‐sulfonium salt ChB catalysis for various ionic transformations, including transfer hydrogenation, bromination, bromolactonization, dimerization of 1,1‐diphenylethylene, nitro‐Michael addition reaction and Ritter reaction. More importantly, the photocapability of ChB was first demonstrated to generate alkynyl radicals for the synthesis of a variety of chalcogenoacetylenes. Mechanistic studies shed light on the mechanism of the photoinduced reactions and confirmed the involvement of alkynyl radicals which are difficult to generate otherwise. Alkynyl sulfonium salts were employed as chalcogen bonding (ChB) catalysts for the first time. They display superior capability in the generation of alkynyl radicals under blue‐light irradiation.
ArticleNumber 202116071
Author Wang, Zhi‐Xiang
Liu, Qiang
Chen, Xiang‐Yu
Lu, Yu
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  organization: University of Chinese Academy of Sciences
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  surname: Wang
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  givenname: Xiang‐Yu
  orcidid: 0000-0002-0383-0910
  surname: Chen
  fullname: Chen, Xiang‐Yu
  email: chenxiangyu20@ucas.ac.cn
  organization: University of Chinese Academy of Sciences
BackLink https://www.ncbi.nlm.nih.gov/pubmed/35118784$$D View this record in MEDLINE/PubMed
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Issue 16
Keywords SULFOXIDES
Alkynyl-Sulfonium Salt
TELLURIDES
Chalcogen Bonding
SELENIDES
Alkynyl Radical
Catalysis
C-H FUNCTIONALIZATION
Chalcogenoacetylenes
EFFICIENT
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  article-title: Recent Perspectives on Rearrangement Reactions of Ylides via Carbene Transfer Reactions
  publication-title: CHEMISTRY-A EUROPEAN JOURNAL
  doi: 10.1002/chem.202002556
SSID ssj0028806
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Snippet Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well‐developed selenium‐ and tellurium‐based salt...
Chalcogen bonding (ChB) has emerged as a promising tool in organic synthesis. However, compared with the well-developed selenium- and tellurium-based salt...
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StartPage e202116071
SubjectTerms Alkynyl Radical
Alkynyl-Sulfonium Salt
Bonding
Bromination
Catalysis
Catalysts
Chalcogen Bonding
Chalcogen bonds
Chalcogenoacetylenes
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Dimerization
Irradiation
Light irradiation
Michael reaction
Physical Sciences
Radiation
Radicals
Salts
Science & Technology
Selenium
Sulfonium salts
Tellurium
Title Alkynyl Sulfonium Salts Can Be Employed as Chalcogen‐Bonding Catalysts and Generate Alkynyl Radicals under Blue‐Light Irradiation
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202116071
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https://www.ncbi.nlm.nih.gov/pubmed/35118784
https://www.proquest.com/docview/2646640694
https://www.proquest.com/docview/2626018721
Volume 61
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