Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives

Sokolova, Olga O.; Bower, John F.

doi:10.1021/acs.chemrev.0c00166

Cited by 110 publications

(72 citation statements)

References 251 publications

(325 reference statements)

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“…As mentioned in the introductory section of this review, the release of the strain of carbocyclic structures is one of the driving forces that can promote the cleavage of C–C bonds [ 26 ], generating intermediates of different nature depending on the experimental conditions which can further evolve intra- or intermolecularly to afford new organic scaffolds. This section presents recent progress carried out on the different approaches where the functionalization of a C–H bond is achieved through the use of cyclopropyl and cyclobutyl scaffolds [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ].…”

Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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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 substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

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Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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“…[42][43][44][45] It is a general building block as well to prepare valuable architectures via ringopening reactions. [46][47][48][49] Herein, we describe the Rh 2 (esp) 2 catalyzed cyclopropanation of N-tosyl substituted enamides with cyclopropenes to construct vicinal trisubstituted cyclopropyl cores with good E/Z and syn/anti stereoselectivities. The small rings were further exploited to undergo regioselectively oxidative ring-opening reactions to deliver conjugated 1,3-dienyl aldehydes under silver and copper co-catalytic systems.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective cyclopropanation of enamides via C–C bond cleavage of cyclopropenes

Chen

Han

et al. 2022

Org. Chem. Front.

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“…Such carboacylation reactions have been extensively demonstrated in strained ring systems. [21][22][23][24][25][26] However, there are only a few known examples of unstrained systems, such as those reported by Douglas and Dong, and the regioselectivity of this reaction remains largely unexplored. [27][28][29][30] Motivated by the importance of directly forming indane rings, we envisioned using ketones as aldehyde surrogates in catalytic C-C activation.…”

Section: Introductionmentioning

confidence: 99%

Regiodivergent Access to 2- or 3-Substituted Indanones: Catalyst-Controlled Carboacylation via C–C Bond Activation

Shao

et al. 2021

CCS Chem

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Indanones are ubiquitous in biologically active compounds. Intramolecular hydroacylation of aldehydes and alkenes is an efficient and atomeconomic route to indane rings. However, these reactions are limited to the transfer of a hydride to the alkene. The transfer of aryl groups enabling the formation of C-C bonds during the cyclization would be a new method for the synthesis of substituted indanones. This report describes the regiodivergent carboacylation of alkenes with ketones to furnish both 2-and 3-substituted indanones in a regiocontrolled manner. The regioselectivity is controlled by the careful selection of different transition-metal catalysts. Moreover, both transformations show high atom economy and good functional group tolerance, which may have implications for C-C bond cleavage in the preparation of complex cyclic molecules.

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Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives

Cited by 110 publications

References 251 publications

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Stereoselective cyclopropanation of enamides via C–C bond cleavage of cyclopropenes

Regiodivergent Access to 2- or 3-Substituted Indanones: Catalyst-Controlled Carboacylation via C–C Bond Activation

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