Elemental Sulfur/Selenium-Mediated Metal-Free Phosphinothioation and Phosphinoselenoation of Vinylsulfonium Salts with P–H Bonds DOI
Biquan Xiong, Meng Li,

Ruzhen Cao

et al.

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

Published: Dec. 16, 2024

An efficient and facile method has been developed for the construction of novel P–S–C P–Se–C bonds by facilitating three-component cross-coupling reaction P–H with elemental sulfur/selenium vinylsulfonium salts, utilizing sodium bicarbonate as a base. This approach eliminates need use toxic odorous active reagents noble metals, thereby offering new pathway synthesizing S-phosphinothioates Se-phosphinoselenoates via organic conversion inorganic sources. The showcased remarkable versatility in terms substrate applicability, particularly organophosphorus compounds containing salt derivatives. resulting phosphinothioation/phosphinoselenoation products can be obtained high yield regioselectivity. Additionally, plausible mechanism this transformation proposed based on step-by-step control experiments 31P NMR tracking analysis.

Language: Английский

Photoinduced, additive- and photosensitizer-free multi-component synthesis of naphthoselenazol-2-amines with air in water DOI

Hong‐Tao Ji,

Keli Wang, Wen‐Tao Ouyang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7983 - 7987

Published: Jan. 1, 2023

An atom- and step-economical, efficient eco-friendly method for constructing naphthoselenazol-2-amines through a visible-light photocatalytic multi-component reaction under aqueous phase conditions is reported.

Language: Английский

Citations

77

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI
Ziyan Zhang, Vladimir Gevorgyan

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

Citations

66

Additive-free synthesis of S-substituted isothioureas via visible-light-induced four-component reaction of α-diazoesters, aryl isothiocyanates, amines and cyclic ethers DOI

Yufen Lv,

Hongyu Ding,

Jinmao You

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 109107 - 109107

Published: Sept. 16, 2023

Language: Английский

Citations

51

Visible light-mediated photolysis of organic molecules: the case study of diazo compounds DOI
Rafael D. C. Gallo, Guilherme Cariello Silva, Tales A. C. Goulart

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(48), P. 7346 - 7360

Published: Jan. 1, 2023

This article discusses the photochemistry of several diazo compounds undergoing visible light-mediated photolysis to generate free carbenes (or other highly reactive intermediates), which can be sequentially trapped by different reacting partners.

Language: Английский

Citations

48

Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

Citations

13

Highlighting multicomponent reactions as an efficient and facile alternative route in the chemical synthesis of organic-based molecules: a tremendous growth in the past 5 years DOI Creative Commons
Reagan L. Mohlala, Thompho Jason Rashamuse,

E. Mabel Coyanis

et al.

Frontiers in Chemistry, Journal Year: 2024, Volume and Issue: 12

Published: Sept. 18, 2024

Since Strecker’s discovery of multicomponent reactions (MCRs) in 1850, the strategy applying an MCR approach has been use for over a century. Due to their ability quickly develop molecular diversity and structural complexity interest, MCRs are considered efficient organic synthesis. Although such as Ugi, Passerini, Biginelli, Hantzsch widely studied, this review emphasizes significance selective elegantly produce compounds potential medicinal chemistry industrial material science applications, well sustainable methods. During synthesis, provide advantages atom economy, recyclable catalysts, moderate conditions, preventing waste, avoiding solvent use. also reduce number sequential multiple one step.

Language: Английский

Citations

10

Hydro-phosphorothiolation of Styrene and Cyclopropane with S-Hydrogen Phosphorothioates under Ambient Conditions DOI

Biswajit Sarkar,

Alakananda Hajra

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5141 - 5145

Published: June 7, 2024

A metal-free hexafluoroisopropanol-mediated hydro-phosphorothiolation of styrenes and donor-acceptor cyclopropanes with

Language: Английский

Citations

9

Chemoselective Synthesis of Unsymmetrical Dithioacetals through Sequential Carbene Insertion and Acetal Exchange of Acylsilanes and Thiols under Visible Light Irradiation DOI
Wang Zhang, Danni Yang,

Dou-Dou Guo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1282 - 1286

Published: Feb. 1, 2024

Dithioacetals are a frequently used motif in synthetic organic chemistry, and most existing reports discuss only symmetrical dithioacetals. Examples of unsymmetrical dithioacetals scarce, few general methods for the selective synthesis these compounds exists. An intriguing visible-light-induced strategy has been established this work sequential reactions S–H insertion acetal exchange between acylsilanes two different thiols that deliver wide variety moderate yields. The were obtained with high selectivity, great functional groups tolerated.

Language: Английский

Citations

6

Synthesis of S-alkyl phosphorothioates/phosphorodithioates via ring-opening reaction of sulfonium salts with S8, H-phosphonates or P4S10, and alcohols DOI
Lihua Yang, Lin Chen,

Bei Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5731 - 5740

Published: Jan. 1, 2024

A simple and practical method for the synthesis of S -alkyl phosphorothioates/phosphorodithioates through three-component reaction cyclic sulfonium salts with 8 , H -phosphonates, or P 4 10 alcohols was readily developed.

Language: Английский

Citations

6

Halide-Free and Metal-Free Allylic Thiolation/Selenation of P(O)H Compounds with Sulfur/Selenium and Allylic Alcohols DOI
Longzhi Zhu, Weiwei Luo, Furong Guo

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(21), P. 10886 - 10892

Published: Jan. 1, 2024

A halide- and metal-free method for forming C–S/Se–P(O) bonds using allylic alcohols, P(O)H compounds, elemental sulfur/selenium is reported, eliminating the need toxic, odorous, moisture-sensitive starting materials.

Language: Английский

Citations

6