N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• important factors, and the commonly utilized chemicals include thiols [16][17][18], disulfides [19][20][21][22], sulfenyl halides [23][24][25], sulfonamides [26], sulfenate esters [27][28], and methyl(bismethylthio)sulfonium salts [29][30]. Among various organic molecules, aryl sulfides are recognized as

• of aryl sulfides by using the catalyst and the base. A catalytic cycle is shown in Scheme 4. Firstly, electrophilic Pd(TFA)2 generated from Pd(OAc)2 and TFA, which (by C–H functionalization of arene 4) led to intermediate II. Oxidative insertion of intermediate II into the N–S bond of 1 afforded

• -(alkyl/arylthio)succinimides 1 led to aryl sulfides 104 (Scheme 43) [77]. The cross-coupling reaction involves protonation of the succinimide moiety by trifluoroacetic acid (TFA) to create electrophilic thio intermediate I. Nucleophilic attack of arene 103 on I led to target product 104. Also, TFA

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• of A) thioanisole to methyl phenyl sulfoxide and B) various aryl sulfides, using 2D-PdPor-COF, 3D-PdPor-COF, and p-PdPor-CHO. General mechanism for oxidation of amines to imines. Oxidation of secondary amines to imines. Oxidation of secondary amines using Pd-TPFPP as photocatalyst. Oxidative amine

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• aryl sulfides 40 to their corresponding sulfoxides 41 using poly(amino acid)-coated platinum electrodes with moderate yield and good to excellent enantiomeric excess (Scheme 17) [47][48]. Osa and co-workers, in 1994, made an important contribution in the area by developing an enantioselective method

Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

• Emeline Benoit,
• Ahmed Fnaiche and
• Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

• chloride to give the corresponding β-thioaryl ketone 4 [10]. Reacting 2 with epoxides results in the formation of the 1-(β-hydroxy)cyclopropyl aryl sulfides 5 [10] while reaction with formaldehydes [11] or aldehydes [12] affords 1-(arylthio)cyclopropylcarbinyl alcohols 6. Treating 6 with Burgess reagent or

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

• Amrita Das,
• Mitasree Maity,
• Simon Malcherek,
• Burkhard König and
• Julia Rehbein

Beilstein J. Org. Chem. 2018, 14, 2520–2528, doi:10.3762/bjoc.14.228

• triflates [8], and diazonium salts [9]. Typical metals used are palladium [10][11][12][13], copper [14][15][16][17][18][19][20][21], nickel [22][23][24], iron [25][26][27][28][29], cobalt [30][31][32], and rhodium [33][34]. Aryl sulfides are also synthesized by cross coupling of thiols and aryl Grignard

• to the desired product 7. Conclusion In conclusion, we have developed a photocatalytic method for the synthesis of aryl sulfides via a radical–radical cation cross coupling of electron rich arenes with aryl and alkyl disulfides. The reaction proceeds at room temperature and avoids the use of

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

• gave better yields than their bromo or chloroanalogues, because of their higher fragmentation stability after single-electron reduction. Disulfides Formation of sulfides Jacobi von Wangelin and co-workers published a photocatalyzed protocol for the formation of aryl sulfides from the respective aryl

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

• Adesh Kumar Singh,
• Varsha Tiwari,
• Kunj Bihari Mishra,
• Surabhi Gupta and
• Jeyakumar Kandasamy

Beilstein J. Org. Chem. 2017, 13, 1139–1144, doi:10.3762/bjoc.13.113

• 1–4). These aryl sulfides underwent oxidation very efficiently to provide the corresponding sulfoxides 1a–4a in excellent yields, i.e., 85–93% under optimized conditions. Similarly, corresponding glycosyl sulfones 1b–4b were also achieved in 91–94% yield by simply altering the reaction conditions as

Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

• can be obtained via reaction of trifluoromethylthiolate with an electrophile like aryl halides. On the other hand, they can also be obtained by reacting aryl sulfides or disulfides under nucleophilic or radical conditions with a trifluoromethylation reagent [16][55][124]. Very recently, several

Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

• Silvia M. Soria-Castro and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2013, 9, 467–475, doi:10.3762/bjoc.9.50

• microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the “one-pot” synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl

• was finally applied to the one-pot three-step synthesis of alkyl aryl sulfides, diaryldisulfides and asymmetric diaryl sulfides. Thus, without isolation, the phenyl thioacetate produced in good yield by the copper-catalyzed reaction of PhI with thioacetate anion 1 was hydrolyzed to the benzene

• thiolate anion by the addition of 2 equiv of KOt-Bu. Different chemical transformations are possible from the arene thiolate ions formed; for example, oxidation to the diaryl disulfide, subsequent nucleophilic substitution reaction with alkyl halides to afford alkyl aryl sulfides, or a second copper

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

• moderate to excellent yields. Keywords: aryl halides; aryl sulfides; copper oxide; cross-coupling; ligand free; potassium thiocyanate; recyclable; Introduction After the discovery of copper-promoted Ullmann reaction [1][2][3] for the construction of carbon-hetero atom bonds, several protocols have been

• reported over the years to establish C–N, C–O, and C–S linkages. Carbon–sulfur bonds are widespread, occurring in numerous pharmaceutically and biologically active compounds [4][5][6][7][8]. A large variety of aryl sulfides are in use for diverse clinical applications in the treatment of cancer [9], HIV

• , bases, solvents, and temperature (Table 1). First, several copper catalysts were screened (Table 1), and CuO was found to be promising for this tandem reaction (Table 1, entry 5). Amongst various bases screened, Cs2CO3 and KOH afforded the symmetrical aryl sulfides in excellent yields (Table 1, entries

Alkene selenenylation: A comprehensive analysis of relative reactivities, stereochemistry and asymmetric induction, and their comparisons with sulfenylation

• Vadim A. Soloshonok and
• Donna J. Nelson

Beilstein J. Org. Chem. 2011, 7, 744–758, doi:10.3762/bjoc.7.85

• -chloroalkyl aryl sulfides and selenides, respectively. Conversely, differences between the two reactions have been reported, but the sources of these differences have not been fully explained: While arenesulfenyl chlorides add to alkenes with an anti-Markovnikov orientation, areneselenenyl chlorides add with

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

• Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

• -process; perfluoroalkylation; perfluoroalkyl sulfides; SRF-introduction; Review 1. Introduction Perfluoroalkyl sulfides of aromatic and heterocyclic compounds have been an important aspect in the general development of organofluorine chemistry over the last twenty years. Alkyl aryl sulfides containing

• other heavy metal fluorides, and even by silver tetrafluoroborate under mild conditions. The halex-method allows the selective preparation of α,α-difluoroalkyl aryl sulfides (and also ethers, sulfoxides and sulfones) as intermediate products in the synthesis of herbicides [66][67]. Interestingly, the