A facile method for hydroxytrifluoromethylation of alkenes with Langlois reagent and DMSO

Shen, Wei-Guo; Wu, Qing-Yan; Gong, Xingyu; Ao, Gui-Zhen; Liu, Feng

doi:10.1039/c9gc00886a

Cited by 48 publications

(13 citation statements)

References 86 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…14 Recently, Liu group have reported that DMSO has been as an oxidant to oxidize CF 3 SO 2 Na to CF 3 radical and provided hydroxyl source at the same time. 15 Based on the fact above, we expected that hydroxysulfenylation of electron-deficient alkenes may be accomplished with high chemoselectivity under metal-and reductant-free conditions in DMSO via alkoxysulfonium ions process.…”

Section: Paper Synthesismentioning

confidence: 99%

DMSO-Mediated Difunctionalization of Electron-Deficient Olefins to Access β-Hydroxysulfides with High Chemoselectivity

et al. 2022

View full text Add to dashboard Cite

A novel and convenient method for the highly chemoselective synthesis of β-hydroxysulfides mediated by DMSO is reported. This eco-friendly reaction was amenable to a broad range of substrates and provided the desired β-hydroxysulfides in moderate to good yields with high selectivity via radical process. Moreover, several pharmaceutical and bioactive molecules were also suitable substrates for this reaction conditions to afford the targeted products in good yields.

show abstract

Section: Paper Synthesismentioning

confidence: 99%

DMSO-Mediated Difunctionalization of Electron-Deficient Olefins to Access β-Hydroxysulfides with High Chemoselectivity

et al. 2022

View full text Add to dashboard Cite

show abstract

“…The reaction was carried out under moisture and oxygen‐free conditions with access to a wide range of β‐trifluoromethyl alcohols (Scheme 19). According to the reported reaction mechanism, trifuoromethyl radical was formed by single‐electron oxidition of Langlois’ reagent, followed by the addition of the radical to the alkene to form a carbon‐centred radical which undergoes further single‐electron oxidation to afford a β‐CF 3 ‐substituted carbocation [61] …”

Section: Application Of Langlois’ Reagent In Organic Transformationsmentioning

confidence: 99%

Recent Advances on the Application of Langlois’ Reagent in Organic Transformations

et al. 2021

View full text Add to dashboard Cite

Langlois’ reagent (trifluoromethanesulfinate salt) has been proven to be a valuable reagent for the synthesis of various classes of molecules, mainly trifluoromethylated compounds, in academic, biological and industrial research. Synthetic uses of Langlois’ reagent in organic transformations of aromatic and heteroaromatic compounds, alkenes, alkynes, boronic acids, carboxylic acids, and etc are discussed.This review aims to demonstrate the ongoing utility of Langlois’ reagent in the preparation of various classes of organic compounds. Furthermore, to address the recent collective papers, the current review summarizes and comprehensively describes manuscripts on synthetic applications of Langlois’ reagent since 2015 until today.

show abstract

“… 12 For example, DMSO has found application in the Swern oxidation, 13 Pfitzner-Moffatt oxidation, 14 Albright-Goldman oxidation, 15 Parikh-Doering oxidation, 16 and other newly reported methods. 17 Most strikingly, DMSO can also be employed as the source of −CH 2 SMe, −SO 2 Me, or −SMe, to afford thio-modified structures. 18 However, a literature survey indicated that the application of DMSO as a sulfur source to introducing −SMe group has remained somewhat underexplored.…”

Section: Introductionmentioning

confidence: 99%

Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

Wang

Ouyang

et al. 2021

J. Org. Chem.

View full text Add to dashboard Cite

A highly substituent-dependent rearrangement allows for the novel and SOCl 2 -induced divergent synthesis of 3-methylthioquinolin-2-ones and 3-methylthiospiro[4.5]trienones through intramolecular electrophilic cyclization of N -aryl propyamides. DMSO acts as both solvent and sulfur source, and use of DMSO- h 6 / d 6 enables the incorporation of SCH 3 or SCD 3 moieties to the 3-position of the heterocyclic framework. Different para -substituents trigger divergent reaction pathways leading to the formation of quinolin-2-ones for mild substituents and spiro[4,5]trienones for both electron-withdrawing and -donating substituents, respectively. On the basis of both computational and experimental results, a new mechanism has been put forward that accounts for the exclusive spirolization/defluorination process and the surprising substituent effects.

show abstract

A facile method for hydroxytrifluoromethylation of alkenes with Langlois reagent and DMSO

Abstract: A simple and mild protocol is developed for the synthesis of β-trifluoromethyl alcohols from alkenes.

Cited by 48 publications

References 86 publications

DMSO-Mediated Difunctionalization of Electron-Deficient Olefins to Access β-Hydroxysulfides with High Chemoselectivity

DMSO-Mediated Difunctionalization of Electron-Deficient Olefins to Access β-Hydroxysulfides with High Chemoselectivity

Recent Advances on the Application of Langlois’ Reagent in Organic Transformations

Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones

Contact Info

Product

Resources

About