Cleavage of carbon-carbon bonds by radical reactions

In recent years, radical C-C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic processes. However, to date radical C-C bond cleavage/functionalization reactions have not been the subject of a dedicated review. Herein we su...

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Published inChemical Society reviews Vol. 48; no. 9; pp. 2615 - 2656
Main Authors Sivaguru, Paramasivam, Wang, Zikun, Zanoni, Giuseppe, Bi, Xihe
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 07.05.2019
Subjects
Carbon
chemical bonding
Chemical bonds
Cleavage
cleavage (chemistry)
Reaction mechanisms
Transformations
Online AccessGet full text
ISSN0306-0012
1460-4744
1460-4744
DOI10.1039/c8cs00386f

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Abstract In recent years, radical C-C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic processes. However, to date radical C-C bond cleavage/functionalization reactions have not been the subject of a dedicated review. Herein we summarize the most recent and significant developments in the radical activation and functionalization of carbon-carbon bonds, with an emphasis on both synthetic outcomes and reaction mechanisms, and highlight how these radical C-C bond cleavage reactions enable challenging transformations. This review provides insights into the in situ generated radicals triggered carbon-carbon bond cleavage reactions.
AbstractList In recent years, radical C-C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic processes. However, to date radical C-C bond cleavage/functionalization reactions have not been the subject of a dedicated review. Herein we summarize the most recent and significant developments in the radical activation and functionalization of carbon-carbon bonds, with an emphasis on both synthetic outcomes and reaction mechanisms, and highlight how these radical C-C bond cleavage reactions enable challenging transformations. This review provides insights into the in situ generated radicals triggered carbon-carbon bond cleavage reactions.
In recent years, radical C–C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic processes. However, to date radical C–C bond cleavage/functionalization reactions have not been the subject of a dedicated review. Herein we summarize the most recent and significant developments in the radical activation and functionalization of carbon–carbon bonds, with an emphasis on both synthetic outcomes and reaction mechanisms, and highlight how these radical C–C bond cleavage reactions enable challenging transformations.
In recent years, radical C-C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic processes. However, to date radical C-C bond cleavage/functionalization reactions have not been the subject of a dedicated review. Herein we summarize the most recent and significant developments in the radical activation and functionalization of carbon-carbon bonds, with an emphasis on both synthetic outcomes and reaction mechanisms, and highlight how these radical C-C bond cleavage reactions enable challenging transformations.In recent years, radical C-C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic processes. However, to date radical C-C bond cleavage/functionalization reactions have not been the subject of a dedicated review. Herein we summarize the most recent and significant developments in the radical activation and functionalization of carbon-carbon bonds, with an emphasis on both synthetic outcomes and reaction mechanisms, and highlight how these radical C-C bond cleavage reactions enable challenging transformations.
Author Sivaguru, Paramasivam
Zanoni, Giuseppe
Bi, Xihe
Wang, Zikun
AuthorAffiliation Department of Chemistry
Northeast Normal University
University of Pavia
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis
AuthorAffiliation_xml – name: Department of Chemistry
– name: University of Pavia
– name: Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis
– name: Northeast Normal University
Author_xml – sequence: 1
  givenname: Paramasivam
  surname: Sivaguru
  fullname: Sivaguru, Paramasivam
– sequence: 2
  givenname: Zikun
  surname: Wang
  fullname: Wang, Zikun
– sequence: 3
  givenname: Giuseppe
  surname: Zanoni
  fullname: Zanoni, Giuseppe
– sequence: 4
  givenname: Xihe
  surname: Bi
  fullname: Bi, Xihe
BackLink https://www.ncbi.nlm.nih.gov/pubmed/30901020$$D View this record in MEDLINE/PubMed
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Notes Xihe Bi started his independent research at the Northeast Normal University (China) at the end of 2008. Professor Bi's research team currently focuses on silver catalysis in organic synthesis. He has received honours and awards including the Young Scholar of the Changjiang Scholars Programme of China (2016), NSFC Foundation for Excellent Young Scientist (2015), Thieme Chemistry Journals Award (2014), and Alexander von Humboldt research fellowship (2006).
Zikun Wang received his BSc from Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, in 2014. Then he worked as a research associate at Changchun Institute of Applied Chemistry, Chinese Academy of Sciences (China). In 2018, Wang joined the Department of Chemistry at Northeast Normal University (China), where he is now an Associate Professor. His research interests concern transition-metal-catalyzed transformations of alkynes.
Paramasivam Sivaguru was born and brought up in Cuddalore, India, and received his BSc from Periyar Arts College (Cuddalore) affiliated to Thiruvalluvar University (India) in 2007. Then he moved to Periyar University (India), where he completed his MSc (2009), MPhil (2010) and PhD (2016) degrees under the direction of Professor A. Lalitha. He then joined as a postdoctoral researcher in the group of Professor Xihe Bi at Northeast Normal University (China) in 2017. His research interests include transition-metal-catalyzed activation of inert bonds.
Giuseppe Zanoni received his BSc and PhD in chemistry from the University of Pavia, Italy. He also worked as a postdoc with BM Trost at Stanford University. After two years devoted to combinatorial chemistry at SmithKline-Beecham in Milan, he moved back to the University of Pavia, where he was promoted to an Associate Professor in 2011. His scientific interests are in the area of asymmetric synthesis, organometallic chemistry, novel PET probes, medicinal chemistry, and natural product chemistry.
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Snippet In recent years, radical C-C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic...
In recent years, radical C–C bond cleavage reactions have been increasingly understood and used to perform transformations that complement traditional ionic...
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SubjectTerms Carbon
chemical bonding
Chemical bonds
Cleavage
cleavage (chemistry)
Reaction mechanisms
Transformations
Title Cleavage of carbon-carbon bonds by radical reactions
URI https://www.ncbi.nlm.nih.gov/pubmed/30901020
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