Metal-catalyzed regiodivergent organic reactions

Metal-catalyzed regiodivergent reactions allow control over regioselectivity in the synthesis of a wide range of organic products. Starting from the same material, it is possible to prepare different regioisomers just by appropriately choosing the catalyst or by modifying the reaction conditions. Th...

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Published inChemical Society reviews Vol. 48; no. 16; pp. 4515 - 4618
Main Authors Nájera, Carmen, Beletskaya, Irina P, Yus, Miguel
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 12.08.2019
Subjects
Carbon
carbon-hydrogen bond activation
catalysts
catalytic activity
chemical bonding
Chemical reactions
Couplings
Lewis bases
Organic chemistry
positional isomers
Regioselectivity
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Abstract Metal-catalyzed regiodivergent reactions allow control over regioselectivity in the synthesis of a wide range of organic products. Starting from the same material, it is possible to prepare different regioisomers just by appropriately choosing the catalyst or by modifying the reaction conditions. Therefore, these regiodivergent methodologies should be included as the key factor in the concept of efficiency and atom economy in synthetic organic chemistry. The synthetic potential of this subject has been demonstrated mainly in addition reactions to unsaturated carbon-carbon bonds, allylic and propargylic nucleophilic substitutions, C-H activation reactions, cross-couplings, and intramolecular or intermolecular cyclizations. This review article overviews the development and rationalization of regiodivergence in these fundamental reactions in the last 15 years. This review discusses metal-catalysed regiodivergent additions, allylic substitutions, CH-activation, cross-couplings and intra- or intermolecular cyclisations.
AbstractList Metal-catalyzed regiodivergent reactions allow control over regioselectivity in the synthesis of a wide range of organic products. Starting from the same material, it is possible to prepare different regioisomers just by appropriately choosing the catalyst or by modifying the reaction conditions. Therefore, these regiodivergent methodologies should be included as the key factor in the concept of efficiency and atom economy in synthetic organic chemistry. The synthetic potential of this subject has been demonstrated mainly in addition reactions to unsaturated carbon–carbon bonds, allylic and propargylic nucleophilic substitutions, C–H activation reactions, cross-couplings, and intramolecular or intermolecular cyclizations. This review article overviews the development and rationalization of regiodivergence in these fundamental reactions in the last 15 years.
Metal-catalyzed regiodivergent reactions allow control over regioselectivity in the synthesis of a wide range of organic products. Starting from the same material, it is possible to prepare different regioisomers just by appropriately choosing the catalyst or by modifying the reaction conditions. Therefore, these regiodivergent methodologies should be included as the key factor in the concept of efficiency and atom economy in synthetic organic chemistry. The synthetic potential of this subject has been demonstrated mainly in addition reactions to unsaturated carbon-carbon bonds, allylic and propargylic nucleophilic substitutions, C-H activation reactions, cross-couplings, and intramolecular or intermolecular cyclizations. This review article overviews the development and rationalization of regiodivergence in these fundamental reactions in the last 15 years.Metal-catalyzed regiodivergent reactions allow control over regioselectivity in the synthesis of a wide range of organic products. Starting from the same material, it is possible to prepare different regioisomers just by appropriately choosing the catalyst or by modifying the reaction conditions. Therefore, these regiodivergent methodologies should be included as the key factor in the concept of efficiency and atom economy in synthetic organic chemistry. The synthetic potential of this subject has been demonstrated mainly in addition reactions to unsaturated carbon-carbon bonds, allylic and propargylic nucleophilic substitutions, C-H activation reactions, cross-couplings, and intramolecular or intermolecular cyclizations. This review article overviews the development and rationalization of regiodivergence in these fundamental reactions in the last 15 years.
Metal-catalyzed regiodivergent reactions allow control over regioselectivity in the synthesis of a wide range of organic products. Starting from the same material, it is possible to prepare different regioisomers just by appropriately choosing the catalyst or by modifying the reaction conditions. Therefore, these regiodivergent methodologies should be included as the key factor in the concept of efficiency and atom economy in synthetic organic chemistry. The synthetic potential of this subject has been demonstrated mainly in addition reactions to unsaturated carbon-carbon bonds, allylic and propargylic nucleophilic substitutions, C-H activation reactions, cross-couplings, and intramolecular or intermolecular cyclizations. This review article overviews the development and rationalization of regiodivergence in these fundamental reactions in the last 15 years. This review discusses metal-catalysed regiodivergent additions, allylic substitutions, CH-activation, cross-couplings and intra- or intermolecular cyclisations.
Author Nájera, Carmen
Beletskaya, Irina P
Yus, Miguel
AuthorAffiliation Universidad de Alicante
Chemistry Department
M. V. Lomonosov Moscow State University
Centro de Innovación en Química Avanzada (ORFEO-CINQA)
AuthorAffiliation_xml – sequence: 0
  name: Centro de Innovación en Química Avanzada (ORFEO-CINQA)
– sequence: 0
  name: M. V. Lomonosov Moscow State University
– sequence: 0
  name: Chemistry Department
– sequence: 0
  name: Universidad de Alicante
Author_xml – sequence: 1
  givenname: Carmen
  surname: Nájera
  fullname: Nájera, Carmen
– sequence: 2
  givenname: Irina P
  surname: Beletskaya
  fullname: Beletskaya, Irina P
– sequence: 3
  givenname: Miguel
  surname: Yus
  fullname: Yus, Miguel
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31282495$$D View this record in MEDLINE/PubMed
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Notes Professor Miguel Yus was born in Zaragoza in 1947. He obtained his BSc (1969), MSc (1971), and PhD (1973) from the University of Zaragoza, and he was a postdoctoral fellow at the MPI Mülheim (1974-1975). In 1976, he returned to the University of Oviedo, where he became an Associate Professor (1977) and Full Professor (1987). In 1988, he moved to become a chair in Organic Chemistry at the University of Alicante. He is the co-author of more than 600 papers (and 6 patents) and has supervised 62 doctoral theses and delivered about 250 lectures abroad. He has received more than 25 000 citations (h-index: 73).
Professor Irina P. Beletskaya was born in Leningrado (St. Petersburg). She graduated in 1963 and got her PhD (1958) and DSci (1963) from the Lomonosov Moscow State University (MSU), where she is a Professor of Chemistry since 1971. In 1992, she was elected a full member of the Russian Academy of Sciences. She is the Editor-in-Chief of the Russian Journal of Organic Chemistry for many years. She has published more than 1000 papers, with more than 22 000 citations (h-index: 59). She has supervised more than 100 PhD students and given more than 100 lectures abroad.
Professor Carmen Nájera was born in Nájera (La Rioja) in 1951. She obtained her BSc (1973) from the University of Zaragoza (1973) and PhD from the University of Oviedo (1979). She spent her postdoctoral stays at the ETH (Zurich), as well as the universities of Oxford, Harvard, and Uppsala. She became an Associate Professor (1985) at the University of Oviedo and Full Professor (1993) at the University of Alicante. She is the coauthor of more than 400 papers (h-index: 68), 6 patents, and 30 book chapters; further, she has supervised more than 45 PhD students. In 2012, she was named a full member of the Royal Spanish Academy of Sciences.
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Snippet Metal-catalyzed regiodivergent reactions allow control over regioselectivity in the synthesis of a wide range of organic products. Starting from the same...
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SubjectTerms Carbon
carbon-hydrogen bond activation
catalysts
catalytic activity
chemical bonding
Chemical reactions
Couplings
Lewis bases
Organic chemistry
positional isomers
Regioselectivity
Title Metal-catalyzed regiodivergent organic reactions
URI https://www.ncbi.nlm.nih.gov/pubmed/31282495
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