Merging C–H and C–C bond cleavage in organic synthesis

Metal-catalysed functionalization of a carbon–hydrogen bond can occur selectively even in the presence of ostensibly more reactive functional groups. Such conversions have changed our perceptions of organic chemistry because we can now consider a C–H bond as a functional group, the reactions of whic...

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Published inNature reviews. Chemistry Vol. 1; no. 5
Main Authors Nairoukh, Zackaria, Cormier, Morgan, Marek, Ilan
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 01.05.2017
Nature Publishing Group
Subjects
639/638/403/933
639/638/403/935
Analytical Chemistry
Biochemistry
Cascade chemical reactions
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cleavage
Complexity
Covalent bonds
Functional groups
Hydrogen bonds
Inorganic Chemistry
Molecular structure
Organic Chemistry
Physical Chemistry
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Summary:Metal-catalysed functionalization of a carbon–hydrogen bond can occur selectively even in the presence of ostensibly more reactive functional groups. Such conversions have changed our perceptions of organic chemistry because we can now consider a C–H bond as a functional group, the reactions of which are among the most attractive and powerful means to rapidly add complexity. Another versatile tool in organic synthesis is the metal-catalysed selective cleavage of C–C bonds. Applying both expedient methods in a tandem process would give us an ideal approach to synthesizing complex molecular architectures. The challenge lies in ensuring that the reactions do not interfere with each other; the simultaneous control of both C–H and C–C bond activations is the subject of this Review. The reactions that meet this challenge and enable a selective merger of C–H and C–C bond activations in a one-pot process are discussed. Their realization could afford sophisticated molecular fragments that are otherwise difficult to access. The disconnection of C–H and C–C bonds is an efficient approach to functionalize organic molecules. Particularly useful are transformations in which these two cleavage reactions operate in tandem. This Review describes this tandem strategy and provides examples of its application in synthetic chemistry.
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ISSN:2397-3358
2397-3358
DOI:10.1038/s41570-017-0035