23705-40-0Relevant academic research and scientific papers
An efficient method for the preparation of monoalkylated sulfonamides from unsubstituted sulfonamides and alkyl diphenylphosphinites by oxidation-reduction condensation using trimethylsilylmethyl azide
Aoki, Hidenori,Kuroda, Kiichi,Mukaiyama, Teruaki
, p. 1266 - 1267 (2005)
An efficient method for monoalkylation of unsubstituted sulfonamides was established by using alkyl diphenylphosphinites, sulfonamides and trimethylsilylmethyl azide and the monoalkylated sulfonamides were afforded in good yields under neutral conditions.
Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
Marcyk, Paul T.,Jefferies, Latisha R.,AbuSalim, Deyaa I.,Pink, Maren,Baik, Mu-Hyun,Cook, Silas P.
supporting information, p. 1727 - 1731 (2019/01/21)
The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.
A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines
Huang, Zhongxing,Wang, Chengpeng,Dong, Guangbin
supporting information, p. 5299 - 5303 (2016/04/26)
Described is a new hydrazone-based exo-directing group (DG) strategy developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. Conveniently synthesized from protected primary amines, the hydrazone DGs are shown to site-selectively promote the β-acetoxylation and tosyloxylation via five-membered exo-palladacycles. Amines with a wide scope of skeletons and functional groups are tolerated. Moreover, the hydrazone DG can be readily removed, and a one-pot C-H acetoxylation/DG removal protocol was also discovered. All about the DGs: A hydrazone-based exo-directing group (DG) strategy is developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. The hydrazone DGs can be conveniently installed and removed, and promote β-acetoxylation and tosyloxylation via a five-membered exo-palladacycle. PG=protecting group, Ts=4-toluenesulfonyl.
The mechanism of alkene elimination from protonated toluenesulphonamides generated by electrospray ionisation
Saidykhan, Amie,Ebert, Jenessa,Martin, William H.C.,Gallagher, Richard T.,Bowen, Richard D.
, p. 165 - 173 (2016/11/09)
The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = CnH2n+1 (n = 1-7), CnH2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = CnH2n+1 (n = 1-8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent unless energised by collision. Two general fragmentations are observed: firstly, elimination of an alkene, CnH2n, obtained by hydrogen abstraction from one of the CnH2n+1 alkyl groups on nitrogen; secondly, cleavage to form CH3C6H4SO2+. The mechanism by which an alkene is lost has been probed by studying the variation of the intensity of the [M + H - CnH2n]+ signal with the structure of the alkyl substituent(s) on nitrogen and by monitoring the competition between the loss of different alkenes from protonated unsymmetrical sulphonamides in which two different alkyl groups are attached to nitrogen. This fragmentation is favoured by branching of the alkyl group at the carbon atom directly attached to nitrogen, thus suggesting that it involves a mechanism in which the stability of the cation obtained by stretching the bond connecting the nitrogen atom to the alkyl group is critical. This interpretation also explains the competition between alkene elimination and cleavage to form CH3C6H4SO2+ (and, in some cases, cleavage to form C6H5CH2+ or [C6H5CHCH3]+).
Br?nsted acid-assisted N-alkylation of sulfonamides using ethers as the alkylation reagents
Shi, Wei,Bai, Chun-Mei,Zhu, Kai,Cui, Dong-Mei,Zhang, Chen
, p. 434 - 438 (2014/01/06)
N-Alkylation of sulfonamides using cyclic ethers as alkylation reagents and Br?nsted acid as a catalyst produced pyrrolidine and piperidine derivatives in good yields. When using symmetrical and unsymmetrical ethers as alkylation reagents, mono-N-alkylation of sulfonamides took place to afford the corresponding products.
Metal-free oxidative coupling of amines with sodium sulfinates: A mild access to sulfonamides
Zhao, Jinwu,Xu, Jingxiu,Chen, Jiaxi,Wang, Xiaoqin,He, Minghua
, p. 64698 - 64701 (2015/04/27)
A practical and mild procedure for the preparation of sulfonamides through TBAI-catalyzed oxidative coupling of amines with sodium sulfinates using TBHP as an oxidant was presented. A variety of amines and sodium sulfinates could go through the transformation, without impacting the hydroxyl group. This journal is
Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
Tang, Xiaodong,Huang, Liangbin,Qi, Chaorong,Wu, Xia,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 6102 - 6104 (2013/07/11)
A new and convenient method for the construction of sulfonamides via a copper-catalyzed oxidative coupling between sodium sulfinates and amines with 1 atm O2 or DMSO as the oxidant was described. This method provides efficient and robust synthesis of functional sulfonamides in good yields and excellent chemoselectivity. And detailed mechanistic studies showed that this transformation may go through a single electron transfer (SET) pathway.
Preparation of sulfonamides from N-silylamines
Naredla, Rajasekhar Reddy,Klumpp, Douglas A.
supporting information, p. 5945 - 5947 (2013/10/22)
Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.
Platinum-based catalysts for the hydroamination of olefins with sulfonamides and weakly basic anilines
Karshtedt, Dmitry,Bell, Alexis T.,Tilley, T. Don
, p. 12640 - 12646 (2007/10/03)
Electrophilic Pt(II) complexes catalyze efficient hydroaminations of olefins by sulfonamides and weakly basic anilines. Catalysts include the structurally characterized complex (COD)Pt(OTf)2 (1) and the known dimer [PtCl2(C2H4)]2, activated by AgBF4. Experiments with substituted anilines establish an empirical pKa cutoff (conjugate acid pKa a ≈ = -6) with various para substituents hydroaminate olefins such as cyclohexene in yields greater than 95% at 90 °C. Hydroamination of propylene by p-toluenesulfonamide proceeds with Markovnikov selectivity, suggesting a mechanism that involves olefin activation at Pt. With norbornene and p-toluenesulfonamide as the substrates and 1 as the catalyst, intermediate [(COD)Pt-(norbornene)2][OTf]2 (3) was identified and characterized by 19F and 195Pt NMR spectroscopies and mass spectrometry. Kinetic studies provide the empirical rate law, rate = kobs[Pt][sulfonamide], and are consistent with a mechanism in which attack of a sulfonamide on the Pt-coordinated olefin is the rate-determining step.
