Copper(I) selenophene-2-carboxylate (CuSC) promoted C–S cross-coupling reaction of thiols with aryl iodides

Barros, Olga Soares do Rego; Silva, Francielle Rodrigues; Nunes, Vanessa Loren

doi:10.1080/17415993.2018.1519566

Cited by 4 publications

(3 citation statements)

References 47 publications

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“…Nevertheless, in the literature there are some examples of Cu(III) compounds bearing fluorinated ligands [44–50] . Besides, the OA/RE pathway has been proposed by other authors [51] …”

Section: Mechanistic Considerationsmentioning

confidence: 99%

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C−S Cross‐Coupling Reactions Catalyzed by Well‐Defined Copper and Nickel Complexes

2022

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This review presents well-defined copper and nickel complexes that have been used in the formation of CÀ S bonds. The use of Cu or Ni catalysts represent an advantage in comparison with those based on precious metals such as Pd, by being two of the most abundant metals in the earth's crust and thus cheaper. As can be expected the catalytic activity of the different Cu and Ni complexes is strongly dependent on the nature of the ligands used. Thus, multidentate and strong electron-donating ligands are of common use to design highly active species since such ligands are capable to stabilize species in high oxidation states which are key intermediates in the reaction mechanisms of these processes. This being particular true in the case of copper, where Cu(III) produces unstable and reactive species that require an "extra stabilization" during the reaction mechanism. Hence, the reaction mechanisms using copper and nickel complexes as catalysts are also discussed in this paper, including the role of the different ligands during the catalytic processes. Although there is an increasing number of reports on CÀ S cross coupling reactions, due to the relevance of this transformation, they are often difficult to reproduce and not of general use since the actual catalytic species are not identified. Thus, we hope that this report will help to promote the search and synthesis of new ligands for the design of more active welldefined complexes that can be used as catalysts in a more rational manner in the formation of valuable CÀ S bondcontaining species.

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“…Nevertheless, in the literature there are some examples of Cu(III) compounds bearing fluorinated ligands [44–50] . Besides, the OA/RE pathway has been proposed by other authors [51] …”

Section: Mechanistic Considerationsmentioning

confidence: 99%

“…[44][45][46][47][48][49][50] Besides, the OA/RE pathway has been proposed by other authors. [51] Scheme 8. Possible reaction mechanism for the CÀ S coupling.…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

C−S Cross‐Coupling Reactions Catalyzed by Well‐Defined Copper and Nickel Complexes

2022

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“…Selenophene derivatives have also been used as ligands in coordination chemistry [ 91 , 92 , 93 , 94 , 95 , 96 , 97 ]. After a pre-activation with a halide or an organometallic (B, Li, Mg, Sn or Zn), these compounds can be employed as reagents in the formation of new C-C [ 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 ], C-N [ 108 , 109 , 110 ] and C-S [ 111 ] bonds under Pd or Cu catalysis, through Heck, Stille, Negish, Kumada, Suzuki and Sonogashira coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

et al. 2020

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The selenophene derivatives are an important class of selenium-based heterocyclics. These compounds play an important role in prospecting new drugs, as well as in the development of new light-emitting materials. During the last years, several methods have been emerging to access the selenophene scaffold, employing a diversity of cyclization-based synthetic strategies, involving specific reaction partners and particularities. This review presents a comprehensive discussion on the recent advances in the synthesis of selenophene-based compounds, starting from different precursors, highlighting the main differences, the advantages, and limitations among them.

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Organochalcogen ligands in catalysis of oxidation of alcohols and transfer hydrogenation

et al. 2020

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Copper(I) selenophene-2-carboxylate (CuSC) promoted C–S cross-coupling reaction of thiols with aryl iodides

Cited by 4 publications

References 47 publications

C−S Cross‐Coupling Reactions Catalyzed by Well‐Defined Copper and Nickel Complexes

C−S Cross‐Coupling Reactions Catalyzed by Well‐Defined Copper and Nickel Complexes

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

Organochalcogen ligands in catalysis of oxidation of alcohols and transfer hydrogenation

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