- Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes
-
An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides toN-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, andN-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.
- Amri, Nasser,Wirth, Thomas
-
p. 15961 - 15972
(2021/07/20)
-
- Access to N-cyanosulfoximines by transition metal-free iminations of sulfoxides
-
A transition metal-free synthesis of N-cyanosulfoximines from sulfoxides using N-chlorosuccinimide (NCS) as oxidising agent and cyanamide as nucleophilic amine source is reported. The products are obtained in moderate to excellent yields. The protocol enables an easy access to N-cyanosulfoximines from readily available starting materials under inversion of configuration at a preexisting stereogenic center.
- Dannenberg,Fritze,Krauskopf,Bolm
-
p. 1086 - 1090
(2017/02/10)
-
- Copper-catalyzed N-cyanation of sulfoximines by AIBN
-
The direct copper-catalyzed N-cyanation of sulfoximines was achieved by using AIBN as a safe cyanide source. It represents a simple and environmentally benign procedure for the construction of the N-CN bond. Furthermore, some sec-amines can also be tolera
- Teng, Fan,Yu, Jin-Tao,Zhou, Zhou,Chu, Haoke,Cheng, Jiang
-
p. 2822 - 2826
(2015/03/18)
-
- Radical N-cyanation of sulfoximine through acetonitrile C-CN cleavage
-
A new strategy for the N-cyanation of sulfoximine via radical process has been developed, leading to the desired products in moderate to excellent yields with good functional group tolerance. This procedure provided an alternative pathway to C-CN bond act
- Hu, Weiming,Teng, Fan,Peng, Haibo,Yu, Jintao,Sun, Song,Cheng, Jiang,Shao, Ying
-
supporting information
p. 7056 - 7058
(2015/11/27)
-
- A copper-mediated oxidative N-cyanation reaction
-
Copper-promoted N-cyanation of aliphatic sec-amine by CuCN is achieved via oxidative coupling. This procedure employs O2 as a clean oxidant. Notably, sulfoximines and 1,1,3,3-tetramethylguanidine also worked well in this procedure. Thus, it represents a key progress in the C-N bond formation reaction as well as in the cyanation reaction. This journal is the Partner Organisations 2014.
- Teng, Fan,Yu, Jin-Tao,Jiang, Yan,Yang, Haitao,Cheng, Jiang
-
supporting information
p. 8412 - 8415
(2014/07/22)
-
- Metal-free synthesis of N -cyano-substituted sulfilimines and sulfoximines
-
Starting from the corresponding sulfides, N-cyano sulfoximines can easily be accessed under metal-free conditions via the corresponding N-cyano-substituted sulfilimines. The reaction sequence involves a sulfide imination with cyanogen amide in presence of a base and N-bromosuccinimide (NBS) followed by an m-chloroperoxybenzoic acid (MCPBA) mediated oxidation of the resulting sulfilimine intermediates.
- Pandey, Ankur,Bolm, Carsten
-
experimental part
p. 2922 - 2925
(2010/10/21)
-
- Iodinane- and metal-free synthesis of N-cyano sulfilimines: Novel and easy access of NH-sulfoximines
-
The synthesis of W-cyanosulfilimines can readily be achieved by reaction of the corresponding sulfides with cyanogen amine in the presence of a base and NBS or l2 as halogenating agents. Oxidation followed by C-N bond cleavage affords synthetically useful WH-free sulfoximines.
- Mancheno, Olga Garcia,Bistri, Olivia,Bolm, Carsten
-
p. 3809 - 3811
(2008/02/12)
-