Synthesis of 2-acyl-benzo[1,3-d]selenazoles via domino oxidative cyclization of methyl ketones with bis(2-aminophenyl) diselenide

Balaguez, Renata A.; Betin, Eduardo S.; Barcellos, Thiago; Lenardão, Eder J.; Schumacher, Ricardo F.

doi:10.1039/c6nj03103j

Cited by 9 publications

(2 citation statements)

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“…Benzo[1,2- d :4,3- d ′]di([1,3]selenazole)s have not been reported previously. However, similar structures have been explored, mainly for materials applications, 19 and BDS synthesis could be extrapolated from the known benzoselenazoles. 20 The most active catalyst 4 was constructed from ortho -xylene 14 ( Scheme 1 ).…”

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confidence: 99%

Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

et al. 2017

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confidence: 99%

Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

et al. 2017

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“…However, benzomonoselenazoles (BMS) have been explored previously with regard to their optoelectronic properties and possible applications in the materials sciences. [ ][ ] In the most active chalcogen‐bonding BDS catalyst reported so far, i.e . 1 , the BDS scaffold is decorated with electron‐withdrawing cyano and sulfone acceptors to deepen the σ holes on the endocyclic Se donors ( Figure ,g ) .…”

Section: Methodsmentioning

confidence: 99%

Chalcogen‐Bonding Catalysis: From Neutral to Cationic Benzodiselenazole Scaffolds

Benz

Besnard

Matile

2018

Helvetica Chimica Acta

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Benzodiselenazoles (BDS) are emerging as privileged structures for chalcogen‐bonding catalysis in the focal point of conformationally immobilized σ holes on strong selenium donors in a neutral scaffold. Whereas much attention has been devoted to work out the advantages of selenium compared to the less polarizable sulfur donors, high expectations concerning bidentate, rigid, and neutral scaffolds have been generated with little experimental support. Here we report design, synthesis and evaluation of the necessary catalysts to confirm that i) bidentate BDS are more effective than their monodentate analogs, ii) conformationally immobilized scaffolds are more effective than more flexible ones, iii) cationic BDS scaffolds are more effective than neutral ones, and iv) in dicationic‐bidentate BDS, contributions from chalcogen‐bonding dominate possible contributions from ion‐pairing catalysis. These conclusions result from rate enhancements found for a Ritter‐type anion‐binding reaction and an X‐ray crystal structure of dicationic BDS with a triflate anion bound with highest precision in the focal point of the σ holes.

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1,3-Selenazoles

Sonawane

Koketsu

2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis of 2-acyl-benzo[1,3-d]selenazoles via domino oxidative cyclization of methyl ketones with bis(2-aminophenyl) diselenide

Abstract: The synthesis of unprecedented 2-acyl-benzo[1,3-d]selenazoles is presented using bis(2-aminophenyl) diselenide and aryl methyl ketones under conventional heating and microwave irradiation.

Cited by 9 publications

References 55 publications

Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

Chalcogen‐Bonding Catalysis: From Neutral to Cationic Benzodiselenazole Scaffolds

1,3-Selenazoles

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