Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Copper-Catalyzed Trifluoromethylthiolation of Enamines, Indoles, and β-Keto Esters

Yang, Yudong; Azuma, Ayaka; Tokunaga, Etsuko; Yamasaki, Mikio; Shiro, Motoo; Shibata, Norio

doi:10.1021/ja402455f

Cited by 309 publications

(124 citation statements)

References 59 publications

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“…128 These reactions have a complex mechanism involving in situ reduction of the trifluoromethanesulfonyl group in the presence of a copper catalyst to give the trifluoromethylthio group. The key steps of this mechanism are shown in Scheme 34.…”

Section: Thiotrifluoromethylation Using Iodonium Ylidesmentioning

confidence: 99%

Iodonium ylides in organic synthesis

Yusubov

Yoshimura

Zhdankin³

2016

Arkivoc

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This review summarizes the chemistry of iodonium ylides with emphasis on their synthetic applications. The preparation, structure and chemistry of iodonium ylides of different structural types are overviewed. Iodonium ylides have found synthetic application as efficient carbene precursors, especially useful as reagents for cyclopropanation of alkenes and preparation of heterocyclic compounds. Recently iodonium ylides have been utilized as efficient reagents in the thiotrifluoromethylation and nucleophilic fluorination reactions.

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Section: Thiotrifluoromethylation Using Iodonium Ylidesmentioning

confidence: 99%

Iodonium ylides in organic synthesis

Yusubov

Yoshimura

Zhdankin³

2016

Arkivoc

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“…Later, a trifluoromethanesulfonyl hypervalent iodonium ylide reagent was also successfully employed to trifluoromethylthiolate indoles. 9 Shen et al have also published lately the trifluoromethylthiolation of indoles in mild conditions with their trifluoromethanesulfenate reagent. 10 Very recently, N-trifluoromethylthiosaccharin has been developed and a larger panel of aromatics could be trifluoromethylthiolated with this new reagent.…”

Section: Ar or Hetarmentioning

confidence: 99%

Electrophilic Aromatic Trifluoromethylthiolation with the Second Generation of Trifluoromethanesulfenamide

Alazet

Billard

2014

Synlett

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Direct trifluoromethylthiolation of various aromatic and heteroaromatic compounds, variously substituted, can be performed with the second generation of trifluoromethanesulfenamide via a 'FriedelCrafts-like reaction'. This reaction requires mild conditions with a catalytic amount of protic or Lewis acid. Good results have been obtained, even with aromatic compounds bearing deactivating substituents.

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“…The direct trifluoromethylthiolation methods are based on either electrophilic or nucleophilic pathways. As for heterocyclic scaffolds, such as benzofurans/ benzothiophenes, 12 isocoumarin, 13 indole [14][15][16][17] and oxidine, [18][19][20] they can be trifluoromethylthiolated by N-trifluoromethanesulfanylamides or hypervalent iodine trifluoromethanesulfenate reagent and N-trifluoromethylthiosaccharin. AgSCF3, as the most common SCF3 -containing nucleophilic reagent, 21 plays a key role in trifluoromethylthiolation of various bioactive structures in medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%