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

• low reactivity of these phthalimides, 10 mol % of catalyst was required. Cross-coupling reaction of sulfoximines 44 with N‑(arylthio)succinimides 1 catalyzed by a nanomaterial containing hexagonal boron nitride (h-BN) and γ-cyclodextrin-supported copper(II) acetate (h-BN@γ-CD@Cu(OAc)2) was developed

• by Guo and Wu et al. (Scheme 19) [56]. Employment of a reusable heterogeneous nanomaterial, mild reaction conditions, avoiding the use of any additive, or base, and water/EtOH as a green solvent system were the advantages of this new method. N-Sulfenyl sulfoximines 45 were synthesized as coupling

• functionalization of aryl C(sp2)–H bonds. FeCl3-catalyzed carbosulfenylation of unactivated alkenes. Copper-catalyzed electrophilic thiolation of organozinc halides. h-BN@Copper(II) nanomaterial catalyzed cross-coupling reaction of sulfoximines and N‑(arylthio)succinimide. AlCl3‑mediated cyclization and

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

• Viola Kolaříková,
• Markéta Rybáčková,
• Martin Svoboda and
• Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

• order to obtain enantiomerically pure compounds by enyne metathesis, a diastereoselective approach starting from chiral substrates is by far the most common. It was frequently used in the construction of chiral compounds, e.g., the mansamine framework [27], anatoxin [28] or sulfoximines [29]. A

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

• forms. For example, aryl cyclopropyl sulfones have been used in the preparation of glucokinase (GK) activators for the treatment of type 2 diabetes [1][2][3][4][5] while aryl cyclopropyl sulfoximines have been utilized for the synthesis of modulators of glucokinase regulatory protein (GKRP) [6][7][8

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

• Sambasivarao Kotha,
• Milind Meshram and
• Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

• respective ring-closure products 62a (98%) and 62b (97%). Finally, SM coupling of 8-halo-7-methoxycoumarins 62a,b with (4-methylfuran-3-yl)boronic acid (63) delivered the cross-coupling product 64 (Scheme 9). In another event, Magnier and co-workers [40] described a simple synthetic route to sulfoximines by

Recent advances in copper-catalyzed C–H bond amidation

• Jie-Ping Wan and
• Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

• in the presence of Cu(acac)2 and t-BuOOt-Bu enabled the C–H amidation for the synthesis of N-cyclohexyl amides without using a ligand or an additional solvent. More interestingly, the catalytic method was also efficiently applicable for the N-alkylation of sulfoximines for the synthesis of various

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• ortho-alkoxylation of arylnitriles 19–20 [48], N-methoxybenzamides 21 [49], and acetanilides 22 [50] and in the ortho-acetoxylation of acetanilides 22 [51] and sulfoximines 23 [52] to prepare cross-dehydrogenative C–O coupling products 24–30 (Scheme 6). The alkoxylation of 1-naphthonitrile 20 occurs not

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

• Kei Murakami and
• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34

• -substituted alkynes, such as alkynyl sulfones, sulfoxides, or sulfoximines as electron-deficient alkynes. Xie reported a copper-catalyzed carbomagnesiation of alkynyl sulfone to give the corresponding alkenylmagnesium intermediates (Scheme 2) [39][40]. Interestingly, the stereochemistry of the products was

• product 1c in 59% yield. In contrast, allylmagnesiated intermediate 1d reacted with benzaldehyde to give syn-addition product 1e stereoselectively. Marek reported copper-catalyzed carbometalation of alkynyl sulfoximines and sulfones using organozinc reagents of mild reactivity [41]. Various organozinc

• -catalyzed carbozincation of alkynyl sulfoximines. Scope of rhodium-catalyzed carbozincation of ynamide. Sequential I/Mg/Zn exchange and arylzincation of cyclopropenes. Manganese-catalyzed arylmagnesiation of arylacetylenes. Acceleration effect of additive on chromium-catalyzed arylmagnesiation

Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis

• Marcus Frings,
• Isabelle Thomé and
• Carsten Bolm

Beilstein J. Org. Chem. 2012, 8, 1443–1451, doi:10.3762/bjoc.8.164

• catalysts in high overall yields without affecting the stereohomogeneity of the sulfur-containing core fragment. Keywords: anhydride opening; catalytic asymmetric Biginelli reaction; organocatalysis; sulfoximines; thioureas; Introduction Since their discovery in the middle of the last century

• , sulfoximines 1 (Figure 1) represent an important compound class among the comprehensive group of organosulfur reagents [1][2][3][4]. Being monoaza analogs of sulfones, sulfoximines have fascinated researchers from both academia and industry. Because of their interesting chemical properties and the biological

• activities found for several derivatives, the use of sulfoximines has been explored in numerous applications. For instance, in agricultural chemistry it was discovered that sulfoximines can improve plant growth or act as insecticides in crop protection [5][6][7][8][9]. Further exemplary contributions come

Recent advances in carbocupration of α-heterosubstituted alkynes

• Ahmad Basheer and
• Ilan Marek

Beilstein J. Org. Chem. 2010, 6, No. 77, doi:10.3762/bjoc.6.77

• (toluene, reflux) and a single isomer was still obtained [53]. 1-Alkynyl sulfoximines behave similarly to alkynyl sulfones and the addition of an organocopper reagent usually leads to two isomers in variable amounts. Copper-catalyzed carbozincation to give a single regio- and stereoisomer in excellent

• -isomers. This effect can even be reinforced when an additional chelating unit is present (pyridylSi, phosphonates, sulfoxides, sulfones, sulfoximines). The resulting vinyl copper species can react with a large variety of electrophiles leading to functionalized adducts in a straightforward manner that can

• . Carbocupration with functionalized organocopper species. Carbocupration of alkynyl sulfoxides. Carbocupration of alkynyl sulfones. Carbocupration of alkynyl sulfoximines. Carbocupration of alkynylsilanes. Carbocupration of functionalized alkynylsilanes. Silyl- and stannyl cupration of silyl- and stannylalkynes.

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• Daikin laboratories in 2003. 1-Oxo-1-trifluoromethyl-1λ6-benzo[d]isothiazol-3-one (30), and 1-trifluoromethyl-benzo[1,3,2]dithiazole 1,3,3-trioxide (31) as well as acyclic sulfoximines 32 were synthesized as new trifluoromethylating agents (Scheme 26). It was possible to trifluoromethylate carbanions

The use of chiral lithium amides in the desymmetrisation of N-trialkylsilyl dimethyl sulfoximines

• Matthew J. McGrath and
• Carsten Bolm

Beilstein J. Org. Chem. 2007, 3, No. 33, doi:10.1186/1860-5397-3-33

• Matthew J. McGrath Carsten Bolm Institut für Organische Chemie, Landoltweg 1, RWTH Aachen, Aachen 52074, Germany 10.1186/1860-5397-3-33 Abstract Background Chiral base desymmetrisation of dimethyl sulfoximines could provide a general route to chiral, enantioenriched dialkyl sulfoximines with

• potential for use in asymmetric catalysis. Results Asymmetric deprotonation of N-trialkylsilyl dimethyl sulfoximines with either enantiomer of lithium N,N-bis(1-phenylethyl)amide in the presence of lithium chloride affords enantioenriched sulfoximines on electrophilic trapping. Ketones, ketimines

• dimethyl sulfoximines is possible. Introduction The preparation of enantioenriched sulfoximines is an important goal in synthesis as these S-chiral compounds make interesting ligands for asymmetric catalysis and have been used in the construction of pseudopeptides. [1][2][3][4] Enantiomerically enriched