Cp*Co<sup>III</sup>-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines

Yoshida, Misaki; Kawai, Kentaro; Tanaka, Ryō; Yoshino, Tatsuhiko; Matsunaga, Shigeki

doi:10.1039/c7cc03072j

Cited by 58 publications

(29 citation statements)

References 97 publications

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“…Very recently, Matsunaga 727 and Wang 728 reported the first protocols for Co-catalysed trifluoromethylthiolation of (hetero)aromatic substrates using (PhSO 2 ) 2 NSCF 3 and AgSCF 3 as reactants ( Scheme 120A and B ). In both cases, halogenated solvents had to be used and relatively low yields (<70%) were obtained.…”

Section: Heterocyclic Dgs In C–h Functionalisationmentioning

confidence: 99%

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

et al. 2018

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Section: Heterocyclic Dgs In C–h Functionalisationmentioning

confidence: 99%

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

et al. 2018

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“…[39][40][41][42][43][44][45][46][47] However, to date, anti-aromatic ring-contracted porphyrins have scarcely been reported. Shinokubo and co-workers established methods for the synthesis of norcorroles with anti-aromatic characteristics that are stable compounds under ambient conditions, [48][49][50] but interestingly they show unique reactivity towards nucleophiles. [51,52] In accord with previous research, we also considered the creation of the anti-aromatic boron complexes 6 and 7 from 4·PF 6 and 5·PF 6 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of [14]Oxatriphyrins(2.1.1) and Their Transformation into Ethane‐Bridged Oxatripyrrins by Boron Complexation

et al. 2018

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[14]Oxatriphyrins(2.1.1) incorporating a furan moiety in the macrocycle have been synthesized by intramolecular McMurry coupling of oxatripyrromethane followed by oxidation. The [14]oxatriphyrins(2.1.1) are highly planar structures with 14π‐electron aromaticity, inducing typical porphyrin‐like absorption and fluorescence features. Compared with [14]thiatriphyrin(2.1.1) and arene‐fused oxatriphyrins(2.1.1), arene‐unperturbed [14]oxatriphyrins(2.1.1) exhibit stronger aromatic characteristics and fluorescence properties. The borylation of [14]oxatriphyrins(2.1.1) with dichloro(phenyl)borane resulted in the formation of boron complexes with a reduced olefin bridge. As a result of the reduction, the macrocycles of these boron complexes lost their aromatic properties, although the targeted boron complexes were predicted to have distinct anti‐aromatic properties by DFT calculations. The resultant ethane‐bridged oxatripyrrins exhibit intense emission because of their rigid structures.

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“…Matsunaga/Yoshino and co‐workers have also demonstrated Cp*Co(III)‐catalyzed directed C−H trifluoromethylthiolation of 2‐phenylpyridines and 6‐arylpurines using N ‐(phenylsulfonyl)‐ N ‐((trifluoromethyl)thio)benzenesulfonamide, electrophilic trifluoromethylthiolating reagent with slightly modified conditions (Scheme ). The method is also applicable to gram scale reaction at higher temperature.…”

Section: Construction Of C‐heteroatom Bondmentioning

confidence: 99%

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Ghorai¹,

Anbarasan²

2019

Asian J Org Chem

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Transition-metal-catalyzed CÀ H bond functionalization has emerged as a powerful tool in contemporary organic synthesis. In this aspect, precious metal-based high-valent catalysts have been extensively studied. In the past decade, earth-abundant high-valent Cp*Co(III)-catalysts have emerged as a promising alternative to the expensive transition metals, providing unique selectivity and reactivity. In this Minireview, we summarized important progresses in the area of Cp*Co (III)-catalyzed CÀ H bond functionalization until 2017.[a] Mr. . Alkylation of CÀ H bonds with activated alkene. Scheme 3. Alkylation of CÀ H bonds with activated alkene. Scheme 4. Alkylation of CÀ H bonds with maleimides.Scheme 5. Alkylation of CÀ H bonds of (hetero)arene with maleimide. Scheme 6. Alkylation of CÀ H bonds with unactivated alkenes. Scheme 7. Allylation of CÀ H bonds with allyl carbonates. . Allylation of CÀ H bonds with allyl acetate. Scheme 9. Allylation of CÀ H bonds of arenes with allyl carbonates. Scheme 10. Allylation of CÀ H bonds with allyl alcohol. Scheme 11. Cobalt catalyzed allylation using allyl alcohol. Scheme 12. Cobalt catalyzed allylation with activated allylating reagent. . Cobalt catalyzed selective addition of C2À H bond to C=N bond. Scheme 18. Cobalt catalyzed selective addition of CÀ H bond to isocyanate. Scheme 19. Cobalt(III)-catalyzed aryl and alkenyl CÀ H aminocarbonylation. Scheme 20. Cobalt catalyzed hydroarylation to ketenimines. Scheme 21. Cobalt catalyzed synthesis of pyrroloindolones. Scheme 22. Cobalt catalyzed alkenylation through hydroarylation to alkyne. Co(III)-catalyzed alkenylation. Scheme 24. Cobalt catalyzed alkenylation of heterocyclic moiety. Scheme 25. Cp*Co III -Catalyzed branch-selective hydroarylation of alkynes. Scheme 26. Cobalt catalyzed C(sp 3 )À H alkenylation. . Cobalt(III)-catalyzed amidation with dioxazolone. Scheme 40. Mechanism of cobalt catalyzed amidation with dioxazolone. Scheme 41. Cobalt(III)-catalyzed CÀ H bond amidation using dioxazolone.

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Cp*Co^III-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines

Abstract: Cp*CoIII-catalyzed directed C–H trifluoromethylthiolation using N-trifluoromethylthiodibenzenesulfonimide as an electrophilic SCF3 source is described.

Cited by 58 publications

References 97 publications

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

Synthesis of [14]Oxatriphyrins(2.1.1) and Their Transformation into Ethane‐Bridged Oxatripyrrins by Boron Complexation

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

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Cp*CoIII-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines

Abstract: Cp*CoIII-catalyzed directed C–H trifluoromethylthiolation using N-trifluoromethylthiodibenzenesulfonimide as an electrophilic SCF3 source is described.

Cited by 58 publications

References 97 publications

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

Synthesis of [14]Oxatriphyrins(2.1.1) and Their Transformation into Ethane‐Bridged Oxatripyrrins by Boron Complexation

Developments in Cp*CoIII‐Catalyzed C−H Bond Functionalizations

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Cp*Co^III-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations