Electro-/photocatalytic alkene-derived radical cation chemistry: recent advances in synthetic applications

Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and cyclic systems for chemical synthesis. Therefore, the synthetic application of these alkene-derived radical cations represents a powerful and g...

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Published inChemical Society reviews Vol. 51; no. 16; pp. 726 - 7237
Main Authors Luo, Mu-Jia, Xiao, Qiang, Li, Jin-Heng
Format Journal Article
LanguageEnglish
Published London Royal Society of Chemistry 15.08.2022
Subjects
Alkenes
Cations
Chemical synthesis
Coupling
Coupling (molecular)
Electron transfer
Lewis bases
Nucleophiles
Oxidation
Oxidizing agents
Photocatalysis
Radicals
Reaction mechanisms
Single electrons
stoichiometry
Substrates
synthesis
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Abstract Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and cyclic systems for chemical synthesis. Therefore, the synthetic application of these alkene-derived radical cations represents a powerful and green tool that can be used to achieve the functionalization of alkenes partially because the necessity of stoichiometric external chemical oxidants and/or hazardous reaction conditions is eliminated. This review summarizes the recent advances in the synthetic applications of the electro-/photochemical alkene-derived radical cations, emphasizing the key single-electron oxidation steps of the alkenes, the scope and limitations of the substrates, and the related reaction mechanisms. Using electrocatalysis and/or photocatalysis, single electron transfer (SET) oxidation of the C&z.dbd;C bonds in the alkenes occurs, generating the alkene-derived radical cations, which sequentially enables the functionalization of translocated radical cations to occur in two ways: the first involves direct reaction with a nucleophile/radical or two molecules of nucleophiles to realize hydrofunctionalization, difunctionalization and cyclization; and the second involves the transformation of the alkene-derived radical cations into carbon-centered radicals using a base followed by radical coupling or oxidative nucleophilic coupling. This review covers the recent progress in electro-/photo-catalytic alkene-derived radical cation chemistry for organic synthesis, including synthetic strategies, plausible mechanisms and further research outlook.
AbstractList Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and cyclic systems for chemical synthesis. Therefore, the synthetic application of these alkene-derived radical cations represents a powerful and green tool that can be used to achieve the functionalization of alkenes partially because the necessity of stoichiometric external chemical oxidants and/or hazardous reaction conditions is eliminated. This review summarizes the recent advances in the synthetic applications of the electro-/photochemical alkene-derived radical cations, emphasizing the key single-electron oxidation steps of the alkenes, the scope and limitations of the substrates, and the related reaction mechanisms. Using electrocatalysis and/or photocatalysis, single electron transfer (SET) oxidation of the CC bonds in the alkenes occurs, generating the alkene-derived radical cations, which sequentially enables the functionalization of translocated radical cations to occur in two ways: the first involves direct reaction with a nucleophile/radical or two molecules of nucleophiles to realize hydrofunctionalization, difunctionalization and cyclization; and the second involves the transformation of the alkene-derived radical cations into carbon-centered radicals using a base followed by radical coupling or oxidative nucleophilic coupling.
Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and cyclic systems for chemical synthesis. Therefore, the synthetic application of these alkene-derived radical cations represents a powerful and green tool that can be used to achieve the functionalization of alkenes partially because the necessity of stoichiometric external chemical oxidants and/or hazardous reaction conditions is eliminated. This review summarizes the recent advances in the synthetic applications of the electro-/photochemical alkene-derived radical cations, emphasizing the key single-electron oxidation steps of the alkenes, the scope and limitations of the substrates, and the related reaction mechanisms. Using electrocatalysis and/or photocatalysis, single electron transfer (SET) oxidation of the C&z.dbd;C bonds in the alkenes occurs, generating the alkene-derived radical cations, which sequentially enables the functionalization of translocated radical cations to occur in two ways: the first involves direct reaction with a nucleophile/radical or two molecules of nucleophiles to realize hydrofunctionalization, difunctionalization and cyclization; and the second involves the transformation of the alkene-derived radical cations into carbon-centered radicals using a base followed by radical coupling or oxidative nucleophilic coupling. This review covers the recent progress in electro-/photo-catalytic alkene-derived radical cation chemistry for organic synthesis, including synthetic strategies, plausible mechanisms and further research outlook.
Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and cyclic systems for chemical synthesis. Therefore, the synthetic application of these alkene-derived radical cations represents a powerful and green tool that can be used to achieve the functionalization of alkenes partially because the necessity of stoichiometric external chemical oxidants and/or hazardous reaction conditions is eliminated. This review summarizes the recent advances in the synthetic applications of the electro-/photochemical alkene-derived radical cations, emphasizing the key single-electron oxidation steps of the alkenes, the scope and limitations of the substrates, and the related reaction mechanisms. Using electrocatalysis and/or photocatalysis, single electron transfer (SET) oxidation of the C=C bonds in the alkenes occurs, generating the alkene-derived radical cations, which sequentially enables the functionalization of translocated radical cations to occur in two ways: the first involves direct reaction with a nucleophile/radical or two molecules of nucleophiles to realize hydrofunctionalization, difunctionalization and cyclization; and the second involves the transformation of the alkene-derived radical cations into carbon-centered radicals using a base followed by radical coupling or oxidative nucleophilic coupling.
Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and cyclic systems for chemical synthesis. Therefore, the synthetic application of these alkene-derived radical cations represents a powerful and green tool that can be used to achieve the functionalization of alkenes partially because the necessity of stoichiometric external chemical oxidants and/or hazardous reaction conditions is eliminated. This review summarizes the recent advances in the synthetic applications of the electro-/photochemical alkene-derived radical cations, emphasizing the key single-electron oxidation steps of the alkenes, the scope and limitations of the substrates, and the related reaction mechanisms. Using electrocatalysis and/or photocatalysis, single electron transfer (SET) oxidation of the CC bonds in the alkenes occurs, generating the alkene-derived radical cations, which sequentially enables the functionalization of translocated radical cations to occur in two ways: the first involves direct reaction with a nucleophile/radical or two molecules of nucleophiles to realize hydrofunctionalization, difunctionalization and cyclization; and the second involves the transformation of the alkene-derived radical cations into carbon-centered radicals using a base followed by radical coupling or oxidative nucleophilic coupling.Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and cyclic systems for chemical synthesis. Therefore, the synthetic application of these alkene-derived radical cations represents a powerful and green tool that can be used to achieve the functionalization of alkenes partially because the necessity of stoichiometric external chemical oxidants and/or hazardous reaction conditions is eliminated. This review summarizes the recent advances in the synthetic applications of the electro-/photochemical alkene-derived radical cations, emphasizing the key single-electron oxidation steps of the alkenes, the scope and limitations of the substrates, and the related reaction mechanisms. Using electrocatalysis and/or photocatalysis, single electron transfer (SET) oxidation of the CC bonds in the alkenes occurs, generating the alkene-derived radical cations, which sequentially enables the functionalization of translocated radical cations to occur in two ways: the first involves direct reaction with a nucleophile/radical or two molecules of nucleophiles to realize hydrofunctionalization, difunctionalization and cyclization; and the second involves the transformation of the alkene-derived radical cations into carbon-centered radicals using a base followed by radical coupling or oxidative nucleophilic coupling.
Author Xiao, Qiang
Li, Jin-Heng
Luo, Mu-Jia
AuthorAffiliation State Key Laboratory of Applied Organic Chemistry
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle
Key Laboratory of Organic Chemistry of Jiangxi Province
Jiangxi Science & Technology Normal University
Lanzhou University
Henan Normal University
Nanchang Hangkong University
School of Chemistry and Chemical Engineering
AuthorAffiliation_xml – name: School of Chemistry and Chemical Engineering
– name: Key Laboratory of Organic Chemistry of Jiangxi Province
– name: State Key Laboratory of Applied Organic Chemistry
– name: Nanchang Hangkong University
– name: Lanzhou University
– name: Jiangxi Science & Technology Normal University
– name: Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle
– name: Henan Normal University
Author_xml – sequence: 1
  givenname: Mu-Jia
  surname: Luo
  fullname: Luo, Mu-Jia
– sequence: 2
  givenname: Qiang
  surname: Xiao
  fullname: Xiao, Qiang
– sequence: 3
  givenname: Jin-Heng
  surname: Li
  fullname: Li, Jin-Heng
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Notes Mu-Jia Luo was born in Jiangxi Province, People's Republic of China, in 1991. He received his MS degree from Central China Normal University (CCNU) in 2017. He joined Prof. Li's group at Hunan University in 2017, where he completed his PhD under the supervision of Professor Jin-Heng Li in 2021. In the same year, he joined the Jiangxi Science & Technology Normal University as a lecturer. His current research interests are focused on electrochemical synthetic methodologies.
Jin-Heng Li was born in Hunan, P. R. of China. He received his BS from Hunan Normal University in 1994. From 1997 to 2000, he studied at Guangzhou Institute of Chemistry, Chinese Academy of Sciences, where he obtained his MS degree. After completing his PhD studies at the University of Science and Technology of China in 2002, he continued his studies as a postdoctoral fellow at the University of Hong Kong (P. R. of China). In 2002, he joined the faculty at Hunan Normal University as a professor. In 2011, he worked as a professor in the College of Chemistry and Chemical Engineering at Hunan University. Since 2016, he has been working as a professor at Nanchang Hangkong University. His current research interests are focused on radical chemistry and unsaturated hydrocarbon transformation chemistry, especially including C-H oxidative radical functionalization, cross-coupling reaction, and cycloaddition reaction.
Qiang Xiao was born in Shanxi Province, People's Republic of China, in 1975. He obtained his PhD degree from Tsinghua University with Prof. Yufen Zhao in 2003. From 2004 to 2005, he worked as a research fellow with Prof. Tom Brown at the University of Southampton, UK. Presently, he serves as the director of both Key Laboratory of Organic Chemistry in Jiangxi Province and Institute of Organic Chemistry in Jiangxi Science & Technology University. His research mainly focuses on nucleoside chemistry and new heterocycle synthetic methodologies.
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Snippet Alkene-derived radical cations are versatile reactive intermediates and have been widely applied in the construction of complex functionalized molecules and...
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SubjectTerms Alkenes
Cations
Chemical synthesis
Coupling
Coupling (molecular)
Electron transfer
Lewis bases
Nucleophiles
Oxidation
Oxidizing agents
Photocatalysis
Radicals
Reaction mechanisms
Single electrons
stoichiometry
Substrates
synthesis
Title Electro-/photocatalytic alkene-derived radical cation chemistry: recent advances in synthetic applications
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