Useful electrophilic trifluoromethylating agents; S-, Se- and Te-(trifluoromethyl)dibenzo-thio-, -seleno- and -telluro-phenium-3-sulfonates

Umemoto, Teruo; Ishihara, Sumi; Adachi, Kenji

doi:10.1016/0022-1139(95)03253-a

Cited by 55 publications

(24 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Further functional group conversion allowed to get nitro derivatives 40 and sulfonates 34 (Fig. 3, Scheme 31) [101]. Interestingly, the Scheme 30.…”

Section: Trifluoromethylchalcogen Saltsmentioning

confidence: 97%

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Ma¹,

Cahard²

2007

Journal of Fluorine Chemistry

543

177

View full text Add to dashboard Cite

“…Further functional group conversion allowed to get nitro derivatives 40 and sulfonates 34 (Fig. 3, Scheme 31) [101]. Interestingly, the Scheme 30.…”

Section: Trifluoromethylchalcogen Saltsmentioning

confidence: 97%

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Ma¹,

Cahard²

2007

Journal of Fluorine Chemistry

543

177

View full text Add to dashboard Cite

“…S-(Perfluoro-ethyl-, -propyl-, -butyl-, and -octyl)dibenzothiophenium triflates and the corresponding 3-sulfonates were also synthesized in a similar manner to the CF 3 analogs [89,92]. These perfluoroalkyl (C 4,8 ) reagents reacted similarly to the corresponding CF 3 reagents.…”

Section: Development Of O- S- Se- Andmentioning

confidence: 97%

“…We also developed a Zwitter-ion type of power-variable trifluoromethylating agents, S-, Se-, and Te-(trifluoromethyl)dibenzothio-, -seleno-, and -tellurophenium-3-sulfonates 35 and nitro derivative 36 (Scheme 14) [92]. The sulfonation and nitration occurred smoothly.…”

Section: Development Of O- S- Se- Andmentioning

confidence: 98%

Exploration of fluorination reagents starting from FITS reagents

Umemoto

2014

Journal of Fluorine Chemistry

Self Cite

View full text Add to dashboard Cite

“…Further nitration of sulfonate 14 led to a more reactive nitro-substituted derivative 15 ( Scheme 10 ). These reagents allow easy separation of by-products from the desired trifluoromethylated products by simple filtration or washing [ 20 ].…”

Section: Reviewmentioning

confidence: 99%

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

Shibata¹,

Matsnev²,

Cahard³

2010

Beilstein J. Org. Chem.

245

100

View full text Add to dashboard Cite

SummarySince the discovery by Yagupolskii and co-workers that S-trifluoromethyl diarylsulfonium salts are effective for the trifluoromethylation of thiophenolates, the design and synthesis of electrophilic trifluoromethylating reagents have been extensively researched in both academia and industry, due to the significant unique features that trifluoromethylated compounds have in pharmaceuticals, agricultural chemicals, and functional materials. Several effective reagents have been developed by the groups of Yagupolskii, Umemoto, Shreeve, Adachi, Magnier, Togni and Shibata. Due to the high stability and reactivity of these reagents, a series of Umemoto reagents, Togni reagent and Shibata reagent are now commercially available. In this review, we wish to briefly provide a historical perspective of the development of so-called “shelf-stable electrophilic trifluoromethylating reagents”, although this field is in constant development.

show abstract

Useful electrophilic trifluoromethylating agents; S-, Se- and Te-(trifluoromethyl)dibenzo-thio-, -seleno- and -telluro-phenium-3-sulfonates

Cited by 55 publications

References 27 publications

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

Exploration of fluorination reagents starting from FITS reagents

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

Contact Info

Product

Resources

About