A simple and practical NaI-catalyzed direct C-H sulfenylation of arenes has been developed under air. In this reaction, aryl sulfides were obtained in moderate to excellent yields with high regioselectivity from readily available aromatic compounds and aryl/alkyl thiols, even on gram scale. To demonstrate the practicability of this reaction, two bioactive compound skeletons were synthesized in good yields. This method can also be used to late-stage modification of curcumin.

Download full-text PDF

Source
http://dx.doi.org/10.1002/asia.201701163DOI Listing

Publication Analysis

Top Keywords

aryl sulfides
8
sodium iodide
4
iodide nai-catalyzed
4
nai-catalyzed cross-coupling
4
cross-coupling c-s
4
c-s bond
4
bond formation
4
formation oxidative
4
oxidative dehydrogenation
4
dehydrogenation cheap
4

Similar Publications

Collaborative Reduction-Induced Nickel-Catalytic Selective C-S Coupling of Aryl Di/Trithiosulfonates with Aryl Halides.

Org Lett

December 2024

Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, People's Republic of China.

Metal-catalytic conversion of polysulfide reagents is a major challenge in organic synthesis due to its challenging activation modes of multiple S-S bonds. The utilization of aryl di- and trithiosulfonates in nickel-catalyzed reductive coupling with aryl halides has been unexplored. Herein, we unprecedentedly describe PPh and Zn-collaborative reduction-induced nickel-catalytic selective C-S coupling of aryl di/trithiosulfonates with aryl halides to access sulfides over common disulfides or trisulfides.

View Article and Find Full Text PDF
Article Synopsis
  • - The new probe (DN) detects hydrogen sulfide (HS) using a chemical reaction that generates a noticeable color change from yellow to pink and produces red fluorescence in specific conditions.
  • - DN shows excellent performance with a low detection limit of 15.1 nM and a quick response time of 5 minutes, making it effective for sensing HS.
  • - A test kit using paper strips was created for checking meat freshness by detecting HS, and DN can also visualize HS in live cells, aiding research on its link to clinical diseases.
View Article and Find Full Text PDF

Two-Electron Oxidative Atom and Group Transfer Reactions at a Well-Defined Uranium(II) Center.

Angew Chem Int Ed Engl

November 2024

Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China.

The multi-electron redox chemistry of uranium(II) compounds remains largely unexplored. Herein, we report a series of two-electron oxidative atom and group transfer reactions at a well-defined uranium(II) center. The reactions of uranium(II) complexes [M][(TPBN)U] (M=K(2,2,2-cryptand) and K(18-crown-6)(THF)) with pyridine-N-oxide or nitrosobenzene, elemental sulfur/selenium or triphenylphosphine sulfide/selenide, and ditellurium salt led to the isolation of uranium(IV) terminal oxo and chalcogenido complexes [M][(TPBN)UX] (X=O, S, Se, Te).

View Article and Find Full Text PDF

Alkylthiolation of Aryl Halides under Electrochemical Conditions.

J Org Chem

December 2024

School of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing Normal University, Nanjing 210023, China.

Article Synopsis
  • An electrochemical method was created to attach alkyl groups to aryl halides using dialkyl disulfides, magnesium as an anode, and graphite felt as a cathode.
  • The process resulted in moderate to good yields of aryl sulfides and also supported the creation of aryl selenides.
  • This approach offers simple conditions and works well with various functional groups, showing promise for use in organic and drug synthesis.
View Article and Find Full Text PDF

Photo-induced carboxylation of C(sp)-S bonds in aryl thiols and derivatives with CO.

Nat Commun

November 2024

Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, P. R. China.

Aryl thiols have proven to be a useful class of electron donors and hydrogen atom sources in photochemical processes. However, the direct activation and functionalization of C(sp)-S bonds in aryl thiols remains elusive in the field of photochemistry. Herein, a photochemical carboxylation of C(sp)-S bonds in aryl thiols with CO is reported, providing a synthetic route to important aryl carboxylic acids.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!