A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Visible-light-mediated copper photocatalysis for organic syntheses

• Yajing Zhang,
• Qian Wang,
• Zongsheng Yan,
• Donglai Ma and
• Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

• Bissember [91]. In 2013, Peters’ group [86] established the copper-catalyzed C–S cross-coupling between thiols and aryl halides. The mechanistic studies revealed that the reaction runs with the inexpensive precatalyst (CuI) and no ligand co-additive is necessary. In 2014, the same group [85] reported the

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

• Zhonglie Yang,
• Yutong Liu,
• Kun Cao,
• Xiaobin Zhang,
• Hezhong Jiang and
• Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

• pathways has the advantages of mild reaction conditions and a high tolerance to functional groups, which can be exploited for artificial syntheses of biological macromolecules. In 2017, Miyake and colleagues [54] designed a type of C–S cross-coupling reaction initiated by an EDA complex promoted by visible

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• reinvestigated the synthesis of DTT 1 by using a Cu-catalyzed C–S cross-coupling reaction with potassium sulfide (K2S) as sulfur source [29]. The best results for this C–S ring-closure reaction were achieved by reacting 3,3’-diiodo-2,2’-bithiophene (5) [30] with the system K2S and copper iodide (CuI) as catalyst

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• co-workers reported the C–S cross-coupling of aryl iodides, bromides, fluorides and chlorides with aromatic thiols (Scheme 19) [50]. The reaction is catalyzed by [fac-Ir(ppy)3]. First, the aromatic thiolate anion, obtained by deprotonation of the thiol with Cs2CO3 as a base, reductively quenches the

• photocatalytically generated thiyl radical to give the C–S cross-coupling product. The same group reported on a photoredox-catalyzed approach for the difluoromethylation of thiophenols, again applying [fac-Ir(ppy)3] as photocatalyst (Scheme 20) [51]. Herein, they describe a single-electron photoreduction of readily

• thiyl radical addition forms a [NiII] intermediate. A second single-electron reduction by [IrII] yields the respective [NiI] sulfide. After oxidative addition of the aryl iodide to the [NiI] sulfide complex, the respective C–S cross-coupling product is formed via reductive elimination from the [NiIII

Ni nanoparticles on RGO as reusable heterogeneous catalyst: effect of Ni particle size and intermediate composite structures in C–S cross-coupling reaction

• Debasish Sengupta,
• Koushik Bhowmik,
• Goutam De and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 1796–1806, doi:10.3762/bjoc.13.174

• , Jadavpur, Kolkata 700032, India. Fax: +91 33 24730957; Tel: +91 33 23223403 10.3762/bjoc.13.174 Abstract The present work demonstrates the C–S cross-coupling reaction between aryl halides and thiols using nickel nanoparticles (Ni NPs) supported on reduced graphene oxide (Ni/RGO) as a heterogeneous

• catalyst. It is observed that the uniformly dispersed Ni NPs supported on RGO could exhibit excellent catalytic activity in C–S cross-coupling reactions and the catalytic application is generalized with diverse coupling partners. Although the electron-rich planar RGO surface helps in stabilizing the

• catalytic process has been established for the first time, and found to be best in the C–S cross-coupling reaction for Ni(0) and Ni(II) NPs of the average sizes 11–12 nm and 4 nm, respectively. Keywords: C–S cross-coupling; heterogeneous catalyst; Ni nanoparticle; reduced graphene oxide; thioether

Nano copper oxide catalyzed synthesis of symmetrical diaryl sulfides under ligand free conditions

• K. Harsha Vardhan Reddy,
• V. Prakash Reddy,
• A. Ashwan Kumar,
• G. Kranthi and
• Y.V.D. Nageswar

Beilstein J. Org. Chem. 2011, 7, 886–891, doi:10.3762/bjoc.7.101

• K. Harsha Vardhan Reddy V. Prakash Reddy A. Ashwan Kumar G. Kranthi Y.V.D. Nageswar Organic Chemistry Divison-I, Indian Institute of Chemical Technology, Hyderabad-500 607, India 10.3762/bjoc.7.101 Abstract Potassium thiocyanate acts as an efficient sulfur surrogate in C–S cross-coupling

• , entries 1 and 2). The ideal temperature for the reaction was found to be 130 °C. A study was conducted on C–S cross-coupling reaction using various sulfur sources under these conditions (Table 2). Among these sulfur surrogates potassium thiocyanate gave good yields in this C–S cross-coupling reaction

• identity and purity of the product was confirmed by 1H and 13C NMR spectroscopy. Synthesis of symmetrical aryl sulfides catalyzed by copper oxide nanoparticles. Screening of copper sources for the cross-coupling reaction between iodo benzene and potassium thiocyanate.a Nano CuO catalyzed C–S cross-coupling