Abstract:Transition metal catalysis has contributed immensely to C–C bond formation reactions over the last few decades, and alkylation is no exception.
“…Derivatization of aryl-and heteroaryl bio-relevant molecules with alkyl groups are of great interest due to specific roles of alkyl groups in modulation of molecular properties. [118][119][120][121] In this context, recently, the Ackermann group was successfully applied rhodaelectro catalysis for the challenging methylation, ethylation and propylation of (hetero)arenes using trifluoroborates as alkylating agents. [122] The reaction conveniently performed in an undivided cell setup using nBuOH/H 2 O as the reaction media.…”
Rhodium-catalyzed CÀ H activation has emerged as a powerful tool for forging CÀ C and C-heteroatom bonds. Nevertheless, the requirement of stoichiometric chemical oxidants for oxidative transformations significantly hampered the overall sustainability of the CÀ H activation transformations. The emergence of merging transition metal catalysis and electrochemistry, called metalla-electrocatalysis provides an excellent opportunity to construct organic molecules efficiently and sustainably. This review highlights the recent developments of rhodium-catalyzed electrochemical CÀ H activation transformations, challenges and opportunities for future developments.
“…Derivatization of aryl-and heteroaryl bio-relevant molecules with alkyl groups are of great interest due to specific roles of alkyl groups in modulation of molecular properties. [118][119][120][121] In this context, recently, the Ackermann group was successfully applied rhodaelectro catalysis for the challenging methylation, ethylation and propylation of (hetero)arenes using trifluoroborates as alkylating agents. [122] The reaction conveniently performed in an undivided cell setup using nBuOH/H 2 O as the reaction media.…”
Rhodium-catalyzed CÀ H activation has emerged as a powerful tool for forging CÀ C and C-heteroatom bonds. Nevertheless, the requirement of stoichiometric chemical oxidants for oxidative transformations significantly hampered the overall sustainability of the CÀ H activation transformations. The emergence of merging transition metal catalysis and electrochemistry, called metalla-electrocatalysis provides an excellent opportunity to construct organic molecules efficiently and sustainably. This review highlights the recent developments of rhodium-catalyzed electrochemical CÀ H activation transformations, challenges and opportunities for future developments.
“…Switchable divergent reactions are recognized as promising synthetic protocols for constructing N-heterocycle skeletons with heightened structural diversity and complexity, in which the products can be switched as required by changing the substrates or reaction conditions. [15] On the other hand, the C(sp 3 )À N bond cleavage cascade reaction has provided a practical and pliable strategy to develop new synthetic methods for achieving the polycyclic N-heterocycles. [16] Compared with the extensive explorations in the fields of C(sp 2 )À N bond cleavage, [17] the advances in cleavage of C(sp 3 )À N have fallen significantly behind due to the high C(sp 3 )À N bonds dissociation-energy and the inert nature.…”
The divergent synthesis of dihydropyrimidouracil and pyrimidouracil derivatives from N‐uracil amidines and tertiaryamines by an oxidative C(sp3)−N cleavage cascade cyclization reaction is first described. This transformation enables the formation of new C(sp3)−N and C(sp2)−N bonds via the selection of different oxidation conditions. The features of this method include tunable product selectivity, excellent chemoselectivity, readily available starting materials, broad substrate scope, good tolerance of functional groups, and moderate to high yields.
“…The direct activation or functionalization of C–H bonds offers powerful tools for the synthesis of numerous functional molecules. 1 One representative application of such bond transformation is the construction of heterocycles by means of either direct intramolecular or cascade ring formation. 2 Accordingly, as fundamental and highly useful heterocyclic motifs, the indoles and benzofurans have been reported to be accessible by different methods based on the conversion of C–H bonds.…”
The annulation reactions of enaminones with quinonediimides /quinoneimides for the selective synthesis of indoles and 2-aminobenzofurans have been realized. With Zn(II) catalysis, quinonediimides reacted with enaminones to give indoles via...
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