Palladium‐Catalyzed Cross‐Coupling of Styrenes with Aryl Methyl Ketones in Ionic Liquids: Direct Access to Cyclopropanes

Cotugno, Pietro; Monopoli, Antonio; Ciminale, Francesco; Milella, Antonella; Nacci, Angelo

doi:10.1002/anie.201408245

Cited by 44 publications

(34 citation statements)

References 27 publications

(36 reference statements)

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“…8 The reaction, which involves the formal cleavage of two C-H bonds at the α-position of the ketone, is promoted by Pd(OAc)2 and requires stoichiometric amounts of Cu(OAc)2 and an oxygen atmosphere, as well as the use of molten tetrabutylammonium acetate (TBAA) as solvent. The mechanistic hypothesis considers the activation of the α-position of the acetophenone to give an oxa-π-allypalladium complex (scheme 3).…”

Section: (2+1) Annulationsmentioning

confidence: 99%

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

2016

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Abstract:The exponential increase in the number of catalytic transformations that involve a metal-promoted activation of hitherto considered inert C-H bonds is promoting a paradigmatic change in the field of synthetic chemistry. While most reactions involving C-H activations consist of simple functionalizations or additions, recent years have witnessed a boost on related transformations that can be formally considered as cycloaddition processes. These transformations are particularly appealing from a synthetic perspective because they allow the conversion of readily available substrates into highly valuable cyclic products in a rapid and sustainable manner. In many cases, these annulations involve the formation of metallacyclic intermediates that resemble those proposed for standard metalcatalyzed cycloadditions of unsaturated precursors.

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Section: (2+1) Annulationsmentioning

confidence: 99%

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

2016

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“…However, its installation into the molecule is a tedious job. Keeping this problem in mind, Nacci and co-workers developed an unusual double C-H activation in arylmethyl ketones, which upon treatment with styrenes gave cyclopropanated products (Scheme 20) [45]. Similarly, 3-pinanamine is another natural product containing 1° amine and is endowed with intriguing biological activities.…”

Section: C(sp 3 )-H Activation and Functionalizationmentioning

confidence: 99%

Recent advances in the application of group-10 transition metal based catalysts in C–H activation and functionalization

Khan

Haque

Al‐Suti

et al. 2015

Journal of Organometallic Chemistry

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2015) Recent advances in the application of group-10 transition metal based catalysts in C-H activation and functionalization. Journal of Organometallic Chemistry. ISSN 0022-328X (In Press) Link to official URL (if available): http://dx. AbstractThe importance of C-H bond activation in a simple molecule to form a molecule with enhanced functionality can be easily understood from a study of biological processes at a molecular level where, for example, a specific enzyme selectively activates a chemically inert C-H bond and functionalises it to a useful product. This strategy is now being used for large scale industrial processes and has both social and environmental benefits. C-H bond functionalization is also of major importance in catalysis because of the possibility of constructing complex structural motifs from relatively simple precursors. However, functionalization of a chemically inert C-H bond needs specific catalysts or reaction conditions that can selectively activate a particular C-H bond, leaving others intact. To achieve this target, various metal catalyzed or mediated reactions have been employed.Keeping the growing importance of this emerging field in mind, we now present recent advances in the field of C-H activation and functionalization using group 10 transition metal catalysts. Attempts have also been made to discuss the future of group 10 transition metals in catalysis.

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“…For that reason, the discovery in 2014 by Nacci, Monopoli and co-workers of means to deploy them as the 1-Catom sources in [2+1] cycloadditions represented a noteworthy breakthrough. [4] They showed that Pd(OAc)2 and Cu(OAc)2 in aerated tetrabutylammonium acetate at 100°C catalyzed the formation of cyclopropanes from aryl methyl ketones and styrenes. The aryl (or heteroaryl) rings were shown to be essential structural features because aliphatic and other ketone types were unreactive or yielded alternative products.…”

mentioning

confidence: 99%

A Valuable Upgrade to the Portfolio of Cycloaddition Reactions

Walton

2016

Angew Chem Int Ed

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Cycloadditions maintain an aura of scientific glamour because of their almost magical organization of multiple components and because of the elegant orbital symmetry rules that underpin them. Cyclotrimerizations are a sub-group in this reaction portfolio, with [2+2+2] cycloadditions being the most familiar. The archetype of this group is the combination of three alkynes to produce benzenes [Scheme 1, equ.

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Palladium‐Catalyzed Cross‐Coupling of Styrenes with Aryl Methyl Ketones in Ionic Liquids: Direct Access to Cyclopropanes

Cited by 44 publications

References 27 publications

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

Metal‐Catalyzed Annulations through Activation and Cleavage of C−H Bonds

Recent advances in the application of group-10 transition metal based catalysts in C–H activation and functionalization

A Valuable Upgrade to the Portfolio of Cycloaddition Reactions

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