Cited by Photoinitiated by red light (625 nm) iodosulfonylation of internal alkynes to synthesize β-iodovinylsulfones

Recent trends in the synthesis and applications of β-iodovinyl sulfones: a decade of progress DOI

Raju Jannapu Reddy,

Jangam Jagadesh Kumar,

Arram Haritha Kumari

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2492 - 2509

Published: Jan. 1, 2024

Over the past decade, there has been exponential growth in vicinal iodosulfonylation of alkynes using sulfonyl and iodide reactants. This review highlights recent developments β-iodovinyl sulfones their applications organic synthesis.

Language: Английский

Citations

Synthesis of Sulfonylthiophenes through [3+2] Cycloaddition of Pyridinium 1,4-Zwitterionic Thiolates with (E)-β-Iodovinyl Sulfones or Bromoallylsulfones DOI

Shenghong Zhang, Jiali Zhang,

Aijun Lv

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 7, 2025

A novel metal-free [3+2] cycloaddition strategy involving (E)-β-iodovinyl sulfones or bromoallylsulfones and pyridinium 1,4-zwitterionic thiolates for the efficient synthesis of sulfonylthiophenes is presented. This method exhibits good substrate tolerance, catalysis, easily prepared bench-stable substrates. The findings highlight a practical protocol accessing sulfonyl-substituted thiophenes with significant biological chemical relevance, serving as an alternative to traditional metal catalysis oxidation aryl/heteroaryl sulfides.

Language: Английский

Citations

Green and rapid acid-catalyzed ynamide skeletal rearrangement and stereospecific functionalization with anisole derivatives DOI

Mohana Reddy Mutra,

T. L. Chandana,

Yun-Jou Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 8124 - 8133

Published: Jan. 1, 2023

Environmentally friendly acid-catalyzed 2-alkynyl-ynamides (N–Csp) bond cleavage, alkyne migration and stereospecific functionalization with anisole derivatives for the synthesis of challenging indole scaffolds in 5–10 minutes.

Language: Английский

Citations

Synthesis of (E)‐β‐Iodovinyl Sulfones via HI‐mediated Vicinal Iodosulfonylation of Alkynes with Sodium Sulfinates DOI

Zu‐Jia Chen,

Yu Zeng,

Zhonghao Li

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(6)

Published: March 21, 2024

Abstract Hydroiodic acid‐mediated vicinal iodosulfonylation reaction of alkynes with sodium sulfinates is proposed for the synthesis ( E )‐ β ‐iodovinyl sulfones. The method easy to operate, environmentally friendly, using inexpensive and easily available raw materials, giving target products good regio‐ stereoselectivity in satisfactory yields.

Language: Английский

Citations

Photoinitiated by Red Light (λ 625 nm) Iodosulfonylation of Internal Alkynes to Synthesize β-Iodovinyl Sulfones DOI

V. A. Abramov, Maxim A. Topchiy, A. S. Malysheva

et al.

Russian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 59(12), P. 2102 - 2106

Published: Dec. 1, 2023

Abstract A number of β-iodovinyl sulfones were synthesized by direct difunctionalization internal alkynes with arenesulfonyl iodides under irradiation red light (λ max 625 nm) generated an economical LED source. The products obtained in high yields (68–99%) from equimolar amounts the reactants. reaction sulfonyl follows a radical mechanism and provides regioselective method synthesis sulfones.

Language: Английский

Citations

Visible‐Light‐Induced Radical Sulfonylative‐Cyclization Cascade of 1,6‐Enynol Derivatives with Sulfinic Acids: A Sustainable Approach for the Synthesis of 2,3‐Disubstituted Benzoheteroles DOI

Arram Haritha Kumari,

Jangam Jagadesh Kumar,

Nunavath Sharadha

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: April 23, 2024

Benzoheteroles are promising structural scaffolds in the realm of medicinal chemistry, but sustainable synthesis 2,3-difunctionalized benzoheterole derivatives is still high demand. Indeed, we have conceptually rationalized intrinsic reactivity propargylic-enyne systems for flexible construction 2,3-disubstituted benzoheteroles through radical sulfonylative-cyclization cascade under organophotoredox catalysis. We hereby report an efficient visible-light-induced sulfonyl radical-triggered cyclization 1,6-enynols with sulfinic acids dual catalytic influence 4CzIPN and NiBr

Language: Английский

Citations

Transition‐Metal‐Free Annulation of Sulfonyl‐Derived 1,3‐Enynes: Simple and Efficient Construction of 2,4‐Disubstituted Thiophenes and Vinyl Sulfone‐Tethered 1,2,3‐NH‐Triazoles DOI

Nunavath Sharadha,

Arram Haritha Kumari,

Raju Jannapu Reddy

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(8)

Published: May 17, 2024

Abstract Thiophenes and 1,2,3‐ NH ‐triazoles are important frameworks in pharmaceuticals advanced functional materials. Vinyl sulfones also blueprint motifs medicinal chemistry, but hybrid analogues of ‐triazole‐derived from vinyl still need to be explored. In this report, we present an efficient transition‐metal‐free [4+1]‐thioannulation sulfonyl‐tethered 1,3‐enynes with Na 2 S the presence Cs CO 3 generate 2,4‐disubstituted thiophenes good high yields. We established a formal [3+2]‐cycloaddition 1,3‐sulfonylenynes NaN under metal‐ base‐free conditions synthesize sulfone‐containing ‐triazole derivatives moderate The scope these protocols was successfully showcased various types bearing sensitive groups complex structural scaffolds. desired products were readily obtained group tolerance compatibility. Based on existing results control experiments, plausible mechanistic pathways presented.

Language: Английский

Citations

Photoinitiated by red light (625 nm) iodosulfonylation of internal alkynes to synthesize β-iodovinylsulfones DOI

V. A. Abramov, Maxim A. Topchiy, A. S. Malysheva

et al.

Журнал органической химии, Journal Year: 2023, Volume and Issue: 59(12), P. 1620 - 1625

Published: Dec. 15, 2023

Language: Английский

Citations