ChemInform Abstract: Selectfluor‐Mediated Fluorination and C—C Bond Cleavage of Cyclohexene‐Fused Isoxazoline N‐Oxides.

Rajawinslin, R. R.; Raihan, Mustafa J.; Janreddy, Donala; Kavala, Veerababurao; Kuo, Chun‐Wei; Kuo, Ting‐Shen; Chen, Mei‐Ling; He, Chiu‐Hui; Yao, Ching‐Fa

doi:10.1002/chin.201406076

“…Yao and co-workers described the Selectfluor-mediated fluorination/cleavage of isoxazoline Noxides (Scheme 86). 146 The use of an excess of Selectfluor in acetonitrile at room temperature allowed the formation of αfluorinated 1,2-diketones in high yields within very short reaction times.…”

Section: Synthetic Methods For the Monofluorination Of Organic Compoundsmentioning

confidence: 99%

Monofluorination of Organic Compounds: 10 Years of Innovation

Champagne

¹

,

Desroches

²

,

Hamel

³

et al. 2015

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“…7 In the heteroatom-heteroatom (X-Y) bond paradigm, the Yao group reported a ring-opening fluorination using isoxazoline Noxides via O-N bond cleavage (Figure 1C). 8 However, all these methods require the use of highly specific substrates, and fluorinations involving the ring opening of aromatic rings or asymmetric fluorination have not yet been reported.…”

mentioning

confidence: 99%

Ring-Opening Fluorination of Bicyclic Azaarenes

Komatsuda

¹

,

Suto

²

,

Kondo

³

et al. 2021

Preprint

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We have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolopyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall trans-formation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon–fluorine bonds. The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups. Additionally, mechanistic studies and enantioselective fluorination have been examined.

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“…7 In the heteroatom-heteroatom (X-Y) bond paradigm, the Yao group reported a ring-opening fluorination using isoxazoline Noxides via N-O bond cleavage (Figure 1C). 8 However, all these methods require the use of highly specific substrates, and fluorinations involving the ring-opening of aromatic rings or asymmetric fluorination have not yet been reported.…”

mentioning

confidence: 99%

Ring-Opening Fluorination of Bicyclic Azaarenes

Komatsuda

¹

,

Suto

²

,

Kondo

³

et al. 2021

Preprint

0

View full text Add to dashboard Cite

We have discovered a ring-opening fluorination of bicyclic azaarenes. Upon treatment of bicyclic azaarenes such as pyrazolopyridines with electrophilic fluorinating agents, fluorination of the aromatic ring is followed by a ring-opening reaction. Although this overall trans-formation can be classified as an electrophilic fluorination of an aromatic ring, it is a novel type of fluorination that results in construction of tertiary carbon–fluorine bonds. The present protocol can be applied to a range of bicyclic azaarenes, tolerating azines and a variety of functional groups. Additionally, mechanistic studies and enantioselective fluorination have been examined.

show abstract

ChemInform Abstract: Selectfluor‐Mediated Fluorination and C—C Bond Cleavage of Cyclohexene‐Fused Isoxazoline N‐Oxides.

Cited by 5 publications

References 0 publications

Monofluorination of Organic Compounds: 10 Years of Innovation

Monofluorination of Organic Compounds: 10 Years of Innovation

Ring-Opening Fluorination of Bicyclic Azaarenes

Ring-Opening Fluorination of Bicyclic Azaarenes

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