Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups DOI Creative Commons
Yue Liu,

Takashi Okazoe,

Tim Gatzenmeier

et al.

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

Published: Oct. 10, 2024

Abstract Sulfur‐containing functional groups (SFGs) are increasingly important for modern medicinal chemistry and their large structural diversity provides many opportunities lead optimization. In an effort to simplify the access full set of SFGs, we report herein a versatile strategy utilizing (hetero)aryl trityl sulfides (ArSCPh 3 ) as common precursors. We developed mild high yielding Pd‐catalyzed thiotritylation cross‐coupling methodology afford ArSCPh compounds from bromides iodides. Efficient chemoselective derivatizations provided eight different SFGs sulfur(VI) fluorine exchange (SuFEx) hubs, which open up further downstream towards SFGs. Thereby obtainable sulfur motifs include aryl pentafluorides (ArSF 5 ), tetrafluoro‐λ 6 ‐sulfanyl chlorides 4 Cl), sulfonimidoyl fluorides (ArS(O)(NR)F), sulfonyl (ArSO 2 F), sulfonic acids H), sulfinyl (ArSOF), all valuable in drug discovery.

Language: Английский

Cascade Reaction of α-Aryl Vinyl and Propargyl Sulfonium Salts with Carbon Nucleophiles: Synthesis of Functionalized Benzyl and Homoallyl Thioethers DOI
Vilas Manikrao Awchar, Sundarababu Baskaran

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

Published: Jan. 1, 2025

A cascade reaction of α-aryl vinyl and propargyl sulfonium salts with C-nucleophiles afforded functionalized thioethers via Michael addition followed by [2,3]-sigmatropic rearrangement.

Language: Английский

Citations

0
Polyoxometalate-based ionic liquids: efficient reversible phase transformation-type catalysts for thiolation of alcohols to construct C–S bonds DOI
Ji-Kun Li, Junwei Ma,

Chuanping Wei

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(10), P. 4492 - 4500

Published: Jan. 1, 2024

[PIMPS] 3 PW 12 O 40 was used as a reversible phase transformation-type catalyst for the thiolation of alcohols to synthesize series benzyl thioethers and exhibited high activity good recyclability.

Language: Английский

Citations

2
Copper-Catalyzed Thiolation of Hydrazones with Sodium Sulfinates: A Straightforward Synthesis of Benzylic Thioethers DOI
Anand Kumar Pandey,

Shiv Chand,

Anup Sharma

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 88(1), P. 475 - 482

Published: Dec. 15, 2022

A facile and sustainable protocol for the thiolation of hydrazones with sodium sulfinates has been developed in presence CuBr2 DBU DMF to afford diverse benzylic thioethers. Control experiments reveal a radical pathway involving thiyl as key intermediate.

Language: Английский

Citations

11
Copper-Catalyzed Direct Thiolation of Ketones Using Sulfonohydrazides: A Synthetic Route to Benzylic Thioethers DOI
Amardeep R. Jadhao, Sanjay S. Gaikwad

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 14078 - 14087

Published: Sept. 12, 2023

A facile copper-catalyzed sustainable thiolation of ketones with sulfonohydrazides has been designed for the efficient construction benzylic thioethers in excellent yield under mild reaction conditions. The current approach avoids widely used reagent, thiols. commercial availability base and reagents, broad substrate scope, convenient procedure make it an attractive method thioether synthesis.

Language: Английский

Citations

6
Access to thioethers from thiols and alcohols via homogeneous and heterogeneous catalysis DOI Creative Commons
Martyna Markwitz, Klaudiusz Labrzycki,

Laura Azcune

et al.

Scientific Reports, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 23, 2023

Abstract A metal-free dehydrative thioetherification method has been reported, enabling the conversion of various alcohols and thiols into thioethers. By employing triflic acid as a catalyst or utilizing recyclable NAFION® superacid catalyst, these methods significantly improve efficiency practicality sulfide preparation.

Language: Английский

Citations

6
Synthesis of Benzyl Thioethers by C−S Coupling of Benzylic Trimethylammonium Salts and Sulfonyl Chlorides DOI Open Access

Xiujuan Ma,

Haoyu Jin,

Min Zeng

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(43)

Published: Aug. 24, 2023

Abstract A facile and efficient method to synthesize thioethers from sulfonyl chlorides benzylic trimethylammonium salts is presented. This protocol provides a simple direct approach realize the reductive coupling reaction of readily available with benzyl ammonium in presence triphenylphosphine along base via C−N cleavage salts. features mild conditions good substrate compatibility afford moderate yields.

Language: Английский

Citations

1
Metal-free thiolation of sulfonyl hydrazone with thiophenol: synthesis of 4-thio-chroman and diarylmethyl thioethers DOI

Kasim Ali,

I. Chatterjee, Gautam Panda

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(36), P. 7447 - 7458

Published: Jan. 1, 2023

A simple, efficient, and transition metal-free approach was developed for accessing 4-thio-substituted chroman diarylmethyl thioethers from sulfonyl hydrazones. This protocol provides straightforward access to a class of diarylmethane derivatives with good excellent yields. operationally simple exhibited tolerance labile functional groups, providing biologically relevant chemical libraries. safe feasible route is applicable the large-scale synthesis chromans, which are great synthetic interest because their further reaction potential.

Language: Английский

Citations

1
Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups DOI Creative Commons
Yue Liu,

Takashi Okazoe,

Tim Gatzenmeier

et al.

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

Published: Oct. 10, 2024

Abstract Sulfur‐containing functional groups (SFGs) are increasingly important for modern medicinal chemistry and their large structural diversity provides many opportunities lead optimization. In an effort to simplify the access full set of SFGs, we report herein a versatile strategy utilizing (hetero)aryl trityl sulfides (ArSCPh 3 ) as common precursors. We developed mild high yielding Pd‐catalyzed thiotritylation cross‐coupling methodology afford ArSCPh compounds from bromides iodides. Efficient chemoselective derivatizations provided eight different SFGs sulfur(VI) fluorine exchange (SuFEx) hubs, which open up further downstream towards SFGs. Thereby obtainable sulfur motifs include aryl pentafluorides (ArSF 5 ), tetrafluoro‐λ 6 ‐sulfanyl chlorides 4 Cl), sulfonimidoyl fluorides (ArS(O)(NR)F), sulfonyl (ArSO 2 F), sulfonic acids H), sulfinyl (ArSOF), all valuable in drug discovery.

Language: Английский

Citations

0