39149-60-5Relevant articles and documents
Metal-Free Benzylic C?H Amination via Electrochemically Generated Benzylaminosulfonium Ions
Hayashi, Ryutaro,Shimizu, Akihiro,Song, Yetao,Ashikari, Yosuke,Nokami, Toshiki,Yoshida, Jun-Ichi
, p. 61 - 64 (2017)
Electrochemical oxidation of toluene derivatives in the presence of N-tosyldiphenylsulfilimine gave the corresponding benzylaminosulfonium ions, which were treated with tetrabutylammonium iodide under non-electrolytic conditions to give N-tosylbenzylamines. The transformation serves as a metal- and chemical-oxidant-free method for benzylic C?H amination. Because of high oxidation potential of N-tosyldiphenylsulfilimine the present method can be applied to synthesis of various benzylamines from functionalized toluene derivatives.
Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides
Zhang, Xinyu,Lin, Bo,Chen, Jianhui,Chen, Jiajia,Luo, Yanshu,Xia, Yuanzhi
, p. 819 - 825 (2021/02/01)
The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.
Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones
Tang, Jing-Jing,Yu, Xiaoqiang,Wang, Yi,Yamamoto, Yoshinori,Bao, Ming
, p. 16426 - 16435 (2021/05/13)
Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.
Gold(III)-Catalyzed Formal [3 + 2] Annulations of N-Acyl Sulfilimines with Ynamides for the Synthesis of 4-Aminooxazoles
Tian, Xianhai,Song, Lina,Han, Chunyu,Zhang, Cheng,Wu, Yufeng,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 2937 - 2940 (2019/04/30)
A gold-catalyzed formal 1,3-dipolar [3 + 2] annulation using readily accessible N-acyl sulfilimines and ynamides is reported. This reaction includes the cleavage of a N-S bond and subsequent C-O bond formation. In total, 30 oxazole derivatives bearing div
Light-induced ruthenium-catalyzed nitrene transfer reactions: A photochemical approach towards N-Acyl sulfimides and sulfoximines
Bizet, Vincent,Buglioni, Laura,Bolm, Carsten
, p. 5639 - 5642 (2014/06/10)
1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported. Double duty: A one-pot sulfur imidation/oxidation sequence using a single ruthenium complex for both steps was developed (see scheme). Photochemical decarboxylations of 1,4,2-dioxazol-5-ones provide N-acyl nitrenes, which imidate sulfides at ambient temperature. The subsequent oxidation then occurs under mild phase-transfer catalysis conditions. In this manner, N-acyl sulfimides and sulfoximines can be obtained in high yields starting from sulfides.
Photo SN-bond cleavage and related reactions of thianthrene sulfilimine derivatives
Fujita, Tomoyuki,Kamiyama, Hideo,Osawa, Yasushi,Kawaguchi, Hiroyuki,Kim, Bung Ju,Tatami, Atsushi,Kawashima, Wataru,Maeda, Tetsuo,Nakanishi, Atsushi,Morita, Hiroyuki
, p. 7708 - 7716 (2008/02/07)
Several 1- and 2-substituted thianthrene sulfilimine derivatives were prepared and the selectivity toward oxidation and N-tosylimination under several conditions was studied. In the photolysis of trans-5-(N-p-tosyl)iminothianthrene 10-oxide (trans-10), photo isomerization to cis-10 was observed. Further, photoimino-transfer reaction of sulfilimines and their 10-mono- and -dioxide derivatives to sulfides was intensively studied to make clear the ability as nitrene precursors.
Reaction of Chromium (Fischer) Carbenes and Sulfilimines
Alcaide, Benito,Casarrubios, Luis,Dominguez, Gema,Sierra, Miguel A.
, p. 3886 - 3894 (2007/10/02)
The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields.Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield.However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phthalimidylamino groups.A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields.For α,β-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimines nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions.In turn, optically active imidates of the type ArN=C(OR*)Me can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the carbene moiety.The reactions above also occur in the dark but reaction times are considerably longer.N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates.Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.
