A Formal [4+1] Annulation incorporating Styrylogous Aldol Condensation to Access Substituted 2-Styryl-benzofurans

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A styrylogous aldol condensation has been introduced, constructing 2-styryl-benzofurans in high yields. The method's application demonstrated the efficient syntheses of biologically active aminostyryl-benzofurans good overall

Language: Английский

---

Pd(II)-Catalyzed Tandem Cycloannulative-Alkenylation of o-Alkynyl-Phenols/Anilines with (E)-β-Iodovinyl Sulfones: A Direct Strategy To Construct 3-(Vinyl sulfonyl)benzoheterole Derivatives

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8889 - 8903

Published: June 7, 2023

Benzoheteroles and vinyl sulfones are the most promising pharmaceutical relevance motifs, yet hybrid analogues of these scaffolds still need to be explored. We report herein a general highly efficient Pd(OAc)2-catalyzed intramolecular cyclization vinylation o-alkynylphenols/o-alkynylanilines with (E)-β-iodovinyl under mild reaction conditions. A direct C(sp2)–C(sp2) cross-coupling is enabled for diversity-oriented synthesis sulfone-tethered benzofurans indoles in good high yields excellent stereoselectivity. Notably, this tandem process was consistent at gram scale, situ, generation 2-(phenylethynyl)phenol has also been utilized scalable synthesis. Late-stage synthetic transformations were further explored, including isomerization desulfonylative-sulfenylation. Moreover, several control experiments accomplished, we proposed plausible mechanism based on existing experimental results.

Language: Английский

---

Recent Advances in Radical Transformations of Propargylic Alcohols

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2659 - 2677

Published: April 4, 2024

Abstract Propargylic alcohols are regarded as a class of readily available and versatile synthons in organic synthesis. Due to their unique bifunctional character, the transformation propargylic has been widely utilized powerful strategy for construction various functionalized frameworks over past few decades. Recently, radical attracted considerable attention synthetic chemistry. This review summarizes recent progress alcohols. Based on different mechanisms formation underlying these transformations, this divided into four parts: (1) transition‐metal catalyzed transformation; (2) photo‐induced (3) electro‐induced (4) metal‐free or oxidant‐mediated

Language: Английский

---

Five-membered ring systems: Furans and benzofurans

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 175 - 209

Published: Jan. 1, 2024

Language: Английский

---

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

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

---

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

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

---

Developments in the Construction of Benzo[b]thiophenes from 2‐Alkynylthioanisoles by Electrophilic and Radical Cyclization Reactions

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Abstract Benzo[ b ]thiophene moieties are important skeletons which have been widely found in many natural products, pharmaceuticals, as well functionalized materials. 2‐Alkynylthioanisoles, a class of bifunctional compounds bearing methylthio and alkynyl groups, easily accessible from Pd‐catalyzed Sonogashira coupling between 2‐halothioanisoles terminal alkynes, employed synthons the construction benzo[b]thiophenes through an electrophilic or radical pathway. This review summarizes related developments with particular focus on reaction mechanism. We hope it will help future research this area believe that discovery new catalytic systems, industrial synthesis benzo[ ]thiophenes 2‐alkynylthioanisoles be achieved soon.

Language: Английский

---