Oxaziridines and diaziridines have been used as versatile intermediates due to their high ring strain as well as the reactive CÀ O/N bond, for the synthesis of diverse range of nitrogen containing compounds. In the past few decades, numerous novel and handy methodologies on the preparations and utilizations of both the oxaziridines and diaziridines have been developed. In spite of few published reviews in the area (almost a decade back), the synthetic communities have made tremendous progress in their preparations and utilizations. This review has demonstrated the comprehensive advancement in the chemistry of oxaziridines and diaziridines for the last few years (almost a decade). 2.4. Oxaziridines from Ketimines 3. Reactivities of Oxaziridines 3.1. Oxygen Atom Transfer Reactions 3.2. Nitrogen Atom Transfer Reactions 3.3. Rearrangement Reactions of Oxaziridines 3.4. Cycloaddition Reactions 4. Synthesis of Diaziridines 4.1. Diaziridines from Imine Substrates 4.2. Bi-Diaziridines and Monocyclic Diaziridines using Nosyloxycarbamate 4.3. Alkenyl Diaziridines 4.4. Diaziridines using HOSA Reagent 4.5. N-Cyclopropyl Diaziridines 4.6. Synthesis of Diaziridines via Photocatalysis 5. Reactivities of Diaziridines and its Derivatives 6. Diaziridines as Intermediates 7. Conclusions
A visible‐light (456 nm) promoted dual catalytic (cobalt‐/photoredox) method for the direct synthesis of sulfonimidoyl guanidine via three‐component reaction of aryl amine, isonitrile and sulfonimidoyl azide (as nitrene source) is developed. The protocol is fast, mild and provides products with a wide range of substrates in 56–86% yields. Additionally, the replacement of aryl amine with alcohol and thiol as nucleophile leads to the formation of sulfonimidoyl isourea and sulfonimidoyl isothiourea respectively, which are not yet reported in the literature.
Herein, we have introduced sulfonimidoyl azide as a precursor in a Cu‐catalyzed Chan‐Evans‐Lam reaction with aryl boronic acid for the synthesis of N‐aryl sulfonimidamide. The CuCl catalyzed reactions of sulfonimidoyl azides and aryl boronic acids have been proceeded in the presence of triethylamine (Et3N) as base in methanol at room temperature under oxygen atmosphere and resulted moderate to good yields of corresponding products in very short time. The synthetic utilities of N‐aryl sulfonimidamides have been established by iodination reactions and Suzuki‐Miyaura coupling reactions.
Herein,
we have reported a metal-free, mild, and novel protocol
for the synthesis of various triarylmethanes (TRAMs) in moderate to
good yields via the reactions of aryl boronic acids and ortho-hydroxyarylaldehydes in the presence of stoichiometric amounts of
Et3N in dichloroethane at 80 °C. Additionally, the
synthetic utilities of few synthesized TRAMs were proven by carrying
out bromination on the −OH-containing aryl part and followed
by functionalization of bromine through a palladium-catalyzed Suzuki–Miyaura
cross-coupling reaction with arylboronic acids in good yields. The
−OH group was also alkylated and arylated through simple alkylation
and Chan–Lam reaction, respectively.
An efficient, mild, and novel route is developed to synthesize sulfonylurea via the nickel-catalyzed tandem coupling of sulfonyl azide, isocyanide, and water in aqueous media. The sulfonyl azide is expected to act as a nitrene precursor, which upon reaction with isocyanide generates carbodiimide. Herein, water acts as a nucleophile and reacts with carbodiimide to deliver the product. The protocol uses an inexpensive nickel catalyst, environmentally friendly water (as the nucleophile), and room temperature and provides products in moderate to good yields.Note pubs.acs.org/joc
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