Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates

Kafuta, Kevin; Korzun, A. E.; Böhm, Marvin J.; Golz, Christopher; Alcarazo, Manuel

doi:10.1002/ange.201912383

Cited by 14 publications

(3 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More recently, several groups have contributed to establishing intermolecular C−H sulfenylation using sulfoxides as a facile means for accessing sulfonium salts . Within these reports, sulfonium salts have proved effective electrophilic partners in transition metal‐catalysed C−C cross‐couplings . In particular, formal C−H cross‐couplings can occur when C−H sulfenylation and C−C bond formation are carried out in one pot …”

Section: Sulfonium Salts In C−c Bond Formationmentioning

confidence: 99%

Radical C−C Bond Formation using Sulfonium Salts and Light

2020

View full text Add to dashboard Cite

Sulfonium salts are playing an increasingly significant role in contemporary organic synthesis.I n particular,t he generation of radicalsf rom sulfonium salts is af undamental process in Naturea nd has been the subject of investigation for over 50 years. However, general synthetic methods that use sulfonium salts as radical precursors are rare.T he advent of photoredox catalysis hast riggered an upsurge of interesti nt he radical chemistry of sulfonium salts and this review surveys recent applications of aryl-and alkylsulfonium saltsi nl ight-mediated, radical C À C bond formation. 1I ntroduction 2E arly Reports on the Photochemistry of Sulfonium Salts 3S ulfonium Salts in C À CB ond Formation 3.1 TheV alue of Arylsulfonium Salts in Light-Mediated C À CB ondF ormation 3.2 TheP reparation of BenzylsulfoniumSalts and their Reactivity in Light-Mediated C À CB ond Formation 3.3 TheD irect Preparation of Arylsulfonium Salts for Light-Mediated C À CB ond Formation 4C onclusion

show abstract

Section: Sulfonium Salts In C−c Bond Formationmentioning

confidence: 99%

Radical C−C Bond Formation using Sulfonium Salts and Light

2020

View full text Add to dashboard Cite

show abstract

“…Notably, the chemoselective transformation of arylsulfonium salts in the presence of aryl halides has been observed in the Pd-catalyzed Suzuki-type coupling reaction with 5-aryldibenzothiophenium salts. 9e…”

Section: Thianthrenation-enabled Site-selective Functionalization Of ...mentioning

confidence: 99%

Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes

Wang

Chen

2022

Synthesis

View full text Add to dashboard Cite

Site-selective functionalization of simple arenes remains a paramount challenge due to the similarity of multiple C–H bonds in the same molecule with similar steric environment and electronic properties. Recently, the site-selective thianthrenation/phenoxathiination of arenes has become an attractive solution to reach this challenging goal and it has been applied in the late-stage functionalization of various bioactive molecules. This short review aims to summarize recent advances in the site-selective C–H functionalization of arenes via aryl thianthrenium salts, as well as mechanistic insights in the remarkable site-selectivity obtained in thianthrenation step.1 Introduction2 Site-Selective Thianthrenation of Arenes and Mechanistic Insight3 Thianthrenation-Enabled Site-Selective Functionalization of Arenes3.1 Thianthrenation-Enabled C(sp 2)–C Bond Formation Reaction3.2 Thianthrenation-Enabled C(sp 2)–X Bond Formation Reaction4 Conclusion and Outlook

show abstract

“…Recently, Ritter group has demonstrated a series of late‐stage functionalization of arenes via the isolated aryl thianthrenium salts, in which remarkable site‐selectivity was obtained. [ 7‐9 ] Almost at the same timeline, we were developing a transient mediator approach for para ‐selective functionalization of monosubstituted simple arenes, and found thianthrene S ‐oxide (TTSO) and phenoxathiine 10‐oxide could serve as the most selective and efficient mediators via sulfide dication intermediates (Scheme 1a). [ 10a ] Ideally, this approach could provide a powerful alternative strategy providing a remarkable selectivity for a wide range of aromatics.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Pd‐Catalyzed Site‐Selective Borylation of Simple Arenes via Thianthrenation^†

et al. 2020

View full text Add to dashboard Cite

of main observation and conclusion Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.

show abstract

Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates

Cited by 14 publications

References 45 publications

Radical C−C Bond Formation using Sulfonium Salts and Light

Radical C−C Bond Formation using Sulfonium Salts and Light

Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes

Pd‐Catalyzed Site‐Selective Borylation of Simple Arenes via Thianthrenation^†

Contact Info

Product

Resources

About

Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates

Cited by 14 publications

References 45 publications

Radical C−C Bond Formation using Sulfonium Salts and Light

Radical C−C Bond Formation using Sulfonium Salts and Light

Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes

Pd‐Catalyzed Site‐Selective Borylation of Simple Arenes via Thianthrenation†

Contact Info

Product

Resources

About

Pd‐Catalyzed Site‐Selective Borylation of Simple Arenes via Thianthrenation^†