1377585-48-2Relevant articles and documents
Visible light promoted synthesis of N-aroylsulfoximines by oxidative C-H acylation of NH-sulfoximines
Jiang, Wenlong,Huang, Youming,Zhou, Lihong,Zeng, Qingle
, p. 1213 - 1220 (2019)
The visible light-promoted synthesis of N-aroylsulfoximines has been accomplished via an oxidative dehydrogenative coupling at room temperature under air without the addition of a photosensitizer, metal catalyst, or base. This process exhibits good functional group tolerance, allows facile isolation and purification, and affords N-aroylsulfoximines with high efficiency. The efficiency of the newly developed protocol is described in detail with 27 examples with yields ranging from 80% to 96%. Furthermore, the chirality of the NH-sulfoximine is completely maintained in the desired N-aroylsulfoximine product (99% ee).
Visible-Light-Induced N-Acylation of Sulfoximines
Duan, Xuelun,Li, Ming,Qiu, Pan,Song, Wangze,Zheng, Yubin
supporting information, p. 2733 - 2737 (2022/04/19)
A metal-, base-, and additive-free N-acylation of sulfoximines was developed under mild conditions using organic photoredox catalyst. This green strategy featured broad substrate scope, good compatibility with air, and high yields (up to 96%). It could be further applied to amino acid modifications and α-keto N-acyl sulfoximine synthesis without any complicated transformations or operations.
Visible light-induced C-C bond cleavage in a multicomponent reaction cascade allowing acylations of sulfoximines with ketones
Bolm, Carsten,Ma, Ding,Shi, Peng,Tu, Yongliang,Wang, Chenyang,Zhang, Duo
supporting information, p. 8096 - 8101 (2021/10/04)
Visible light induces C-C-bond cleavage reactions of ketones, which can be utilized forN-acylations of sulfoximines. No (photo)catalyst is required, and the reactions occur at ambient temperature in air. The substrate scope is broad for both ketones and sulfoximines. For convertingNH-sulfoximines, the presence of NBS is essential.
Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones
Tang, Jing-Jing,Yu, Xiaoqiang,Wang, Yi,Yamamoto, Yoshinori,Bao, Ming
supporting information, 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.
Harnessing sulfur and nitrogen in the cobalt(iii)-catalyzed unsymmetrical double annulation of thioamides: Probing the origin of chemo- And regio-selectivity
Shankar, Majji,Saha, Arijit,Sau, Somratan,Ghosh, Arghadip,Gandon, Vincent,Sahoo, Akhila K.
, p. 6393 - 6405 (2021/05/19)
An unconventional cobalt(iii)-catalyzed one-pot domino double annulation of aryl thioamides with unactivated alkynes is presented. Sulfur (S), nitrogen (N), and o,o′-C-H bonds of aryl thioamides are involved in this reaction, enabling access to rare 6,6-fused thiopyrano-isoquinoline derivatives. A reverse 'S' coordination over a more conventional 'N' coordination of thioamides to the Co-catalyst specifically regulates the formation of four [C-C and C-S at first and then C-N and C-C] bonds in a single operation, a concept which is uncovered for the first time. The power of the N-masked methyl phenyl sulfoximine (MPS) directing group in this annulation sequence is established. The transformation is successfully developed, building a novel chemical space of structural diversity (56 examples). In addition, the late-stage annulation of biologically relevant motifs and drug candidates is disclosed (17 examples). The preliminary photophysical properties of thiopyrano-isoquinoline derivatives are discussed. Density functional theory (DFT) studies authenticate the participation of a unique 6π-electrocyclization of a 7-membered S-chelated cobaltacycle in the annulation process.
Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions
Ambala, Srinivas,Arvidsson, Per I.,Govender, Thavendran,Kruger, Hendrik G.,Naicker, Tricia,Rajbongshi, Kamal K.
, p. 1279 - 1286 (2020/04/15)
An efficient catalyst-free radical cross-coupling reaction between aromatic aldehydes and sulfoximines was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines in moderate to excellent yields (27 examples). This protocol proved to be rapid, easy to handle, and applicable to a broad scope of substrates.
Method for synthesizing sulfoxide imide acylate
-
Paragraph 0007; 0008; 0009; 0010; 0011-0013; 0038-0040, (2019/04/13)
The invention discloses a method for synthesizing sulfoxide imide acylate by visible light induction under the condition that no metal catalysts are provided, namely sulfoxide imide acylate is prepared under a mild reaction condition and the combined acti
One-Pot Unsymmetrical {[4 + 2] and [4 + 2]} Double Annulations of o/ o′-C-H Bonds of Arenes: Access to Unusual Pyranoisoquinolines
Shankar, Majji,Ghosh, Koushik,Mukherjee, Kallol,Rit, Raja K.,Sahoo, Akhila K.
supporting information, p. 5144 - 5148 (2018/09/13)
With the aid of a transformable sulfoximine directing group, unprecedented one-pot unsymmetrical double annulations {[4 + 2] and [4 + 2]} of hetero(arenes) with alkynes are revealed under Ru(II) catalysis. Functionalization of both ortho-C-H bonds of (hetero)arene is reflected in the building of unusual 6,6-fused pyranoisoquinoline skeletons. Construction of four [(C-C)-(C-N) and (C-C)-(C-O)] bonds occurs in one step under single catalytic conditions. The challenging unsymmetrical double annulations of both o-C-H bonds of arenes with two distinct alkynes is effectively demonstrated. Control experiments and deuterium scrambling findings are shown.
Palladium catalyzed aroylation of NH-sulfoximines with aryl halides using chloroform as the CO precursor
Guo, Sheng-rong,Santhosh Kumar, Pailla,Yuan, Yan-qin,Yang, Ming-hua
supporting information, p. 2681 - 2684 (2017/06/14)
A palladium-catalyzed aroylation of NH-sulfoximines for the efficient synthesis of N-aroyl sulfoximines from aryl halides and chloroform has been developed. The mild reaction conditions (temperature, catalyst loading) and the use of a CO surrogate render this transformation a useful method for the synthesis of N-aroyl sulfoximines from available feedstock.
Copper-catalyzed preparation of N-aroylated sulfoximines from methylarenes
Hou, Anguo,Zhao, Zijian
supporting information, p. 1201 - 1208 (2017/07/06)
A copper-catalyzed methodology for the preparations of N-aroylated sulfoximines from methylarenes was herein demonstrated. The transformation proceeded with the assistance of external oxidant tert-butyl hydroperoxide, requiring for no additional solvents or ligands. The good compatibility and high efficiency of the newly developed protocol were well described by 21 examples and up to 91% yields. Moreover, the protocol was proved by the control reactions to proceed through a radical pathway.
