2020
DOI: 10.3390/molecules25245900
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Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Abstract: The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of subst… Show more

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Cited by 22 publications
(11 citation statements)
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“…In contrast to less strained alkenes, however, there exists a unique challenge in controlling the diverse modes of reactivity (Figure A). Additions to cyclopropenes are known to occur with ring-retention to yield cyclopropyl products, as well as with ring-opening to yield allylic products. In general, ring-retentive hydrofunctionalizations require softer nucleophiles, such as boranes, stannanes, and carbon nucleophiles. Ring-opening hydrofunctionalizations require harder nucleophiles, such as amines, alcohols, or phosphonates. However, there are exceptions to this trend, including Hou’s ring-retentive hydroamination and Yamamoto’s ring-opening addition of carbon nucleophiles …”
Section: Introductionmentioning
confidence: 99%
“…In contrast to less strained alkenes, however, there exists a unique challenge in controlling the diverse modes of reactivity (Figure A). Additions to cyclopropenes are known to occur with ring-retention to yield cyclopropyl products, as well as with ring-opening to yield allylic products. In general, ring-retentive hydrofunctionalizations require softer nucleophiles, such as boranes, stannanes, and carbon nucleophiles. Ring-opening hydrofunctionalizations require harder nucleophiles, such as amines, alcohols, or phosphonates. However, there are exceptions to this trend, including Hou’s ring-retentive hydroamination and Yamamoto’s ring-opening addition of carbon nucleophiles …”
Section: Introductionmentioning
confidence: 99%
“…The most prevalent β-carbon eliminations are driven by release of ring strain. [16][17][18][19][20] The most common examples of this are when cyclic alcohols are used to form metal homoenolate nucleophiles (Scheme 1a). 16 The relief of steric strain via a β-carbon elimination, as seen in the Catellani reaction, rely on the build-up of increasing steric encumbrance during the course of the reaction (Scheme 1b).…”
mentioning
confidence: 99%
“…16 The relief of steric strain via a β-carbon elimination, as seen in the Catellani reaction, rely on the build-up of increasing steric encumbrance during the course of the reaction (Scheme 1b). 17,21,22 Other strategies to enable β-carbon eliminations rely on the formation of a strong π-bond (Scheme 1c). 17,19,[23][24][25][26][27][28][29] These biased systems make it difficult to study the effects of different parameters on the β-carbon elimination process, and thus an unbiased system would not only be conceptually novel, but allow for the examination of other parameters on reversible C-C bond cleavage.…”
mentioning
confidence: 99%
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“…The intermediate could undergo migratory insertion (MI) into an unsaturated unit X = Y, yielding the “sew” product upon reductive elimination (RE). However, the process can be interrupted by either lack of a π unit or by C–H bond activation; hence, a cascade C–C/C–H bond activation is realized (Scheme , reddish arrow). , …”
mentioning
confidence: 99%