594-44-5Relevant articles and documents
Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
supporting information, p. 8338 - 8342 (2021/10/25)
We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
One-pot synthesis of symmetric 1,7-dicarbonyl compounds via a tandem radical addition-elimination-addition reaction
Huang, Zhongyan,Xu, Jiaxi
, p. 15114 - 15120 (2013/09/02)
A novel approach to synthesize symmetric 1,7-dicarbonyl compounds via a tandem radical addition-elimination-addition reaction of S-carbonylmethyl xanthates with allylmethylsulfone and its analogues has been developed. Radicals were produced from S-carbonylmethyl xanthates by adding dilauroyl peroxide and reacted with allylmethylsulfone or analogues to generate terminal olefins as intermediates. The excessive radicals reacted with the intermediate olefins immediately to give adducts of symmetric 1,7-dicarbonyl compounds. This is an efficient method to synthesize 1,7-dicarbonyl compounds under mild conditions. The Royal Society of Chemistry 2013.
Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation
Yang, Zhanhui,Zheng, Yongpeng,Xu, Jiaxi
supporting information, p. 2165 - 2169 (2013/10/22)
A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.
One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
Maleki, Behrooz,Hemmati, Saba,Tayebee, Reza,Salemi, Sirous,Farokhzad, Yasaman,Baghayeri, Mehdi,Zonoz, Farrokhzad Mohammadi,Akbarzadeh, Elahe,Moradi, Rohollah,Entezari, Azam,Abdi, Mohammad Reza,Ashrafi, Samaneh Sedigh,Taimazi, Fereshteh,Hashemi, Majid
, p. 2147 - 2151 (2013/12/04)
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.
Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation
Yang, Zhanhui,Xu, Jiaxi
, p. 1675 - 1682 (2013/07/27)
A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.
Diverse reactions of sulfonyl chlorides and cyclic imines
Liu, Jing,Hou, Shili,Xu, Jiaxi
experimental part, p. 2377 - 2391 (2012/04/04)
Although alkanesulfonyl chlorides react with linear imines to give rise to β-sultam derivatives, in this study, they were reacted with various cyclic imines, including 1-pyrroline, oxazoline, 5,6-dihydro-4H-oxazines and thiazines, 4,5-dihydro-3H-benzo[c]azepine, and 3,4-dihydroisoquinoline, to produce diverse products instead of β-sultam derivatives. The results indicate that alkanesulfonyl chlorides react with cyclic imines to generate N-alkanesulfonyl cyclic iminium ions, which are attacked by nucleophiles, such as water and chloride anion, in the reaction systems, affording addition products. The iminium intermediates cannot undergo a ring closure to form β-sultam derivatives. Arenesulfonyl chlorides showed similar behavior when they reacted with cyclic imines. The scope and limitation of the reaction between sulfonyl chlorides and imines were investigated. Copyright Taylor & Francis Group, LLC.
IMPROVED PROCESS FOR THE SULFOCHLORINATION OF HYDROCARBONS
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Page/Page column 3-4, (2011/02/24)
Produce a sulfo-chlorinated hydrocarbon using liquid sulfur dioxide, a chlorinating agent such as chlorine or sulfuryl chloride, and a metal complex catalyst, the catalyst being represented as LnM where L is at least one of an amine, phosphine, chloride or oxide, n is an integer within a range of from 1 to 6, and M is a metal selected from a group consisting of copper (Cu), ruthenium (Ru), iron (Fe), chromium (Cr), lanthanum (La), nickel (Ni), palladium (Pd), rhodium (Rh), rhenium (Re), molybdenum (Mo) and manganese (Mn).
Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
Veisi, Hojat,Ghorbani-Vaghei, Ramin,Hemmati, Saba,Mahmoodi, Jafar
experimental part, p. 2315 - 2320 (2011/10/13)
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.
Development of an extremely efficient oxidative chlorination reaction: The value of routine data collection
Barnwell, Neil,Cornwall, Philip,Horner, Daniel,Knott, Jason,Liddon, John
supporting information; experimental part, p. 278 - 288 (2010/04/29)
This contribution describes the development of an extremely efficient process for the oxidative chlorination of a benzyl, alkyl thioether to yield an alkylsulfonyl chloride. This process was subsequently run on >100 kg scale. The product alkylsulfonyl chloride was required as an intermediate, being used by several drug projects, to prepare sulfonamides. Routine data collection and reaction profiling has led to understanding, which has allowed an alternative reaction pathway to be exploited for the development of a two-step, oxidation-chlorination process. The scope of this new two-step process was briefly examined. The results of this study have allowed us to propose an empirical method for predicting the course of these oxidative chlorination reactions. During these studies we have developed a simple laboratory rig, constructed from inexpensive, readily available equipment, which allows the controlled accurate delivery of known volumes (100s of milliliters) of chlorine gas at a given rate. In our laboratories, this has made the use of gaseous chlorine a considerably less onerous task. This work is testimony to the fruit which may be borne from attempts to gain process understanding, even of an already high-yielding reaction.
Chlorotrimethylsilane-nitrate salts as oxidants: Direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Olah, George A.
, p. 5847 - 5850 (2008/02/09)
(Chemical Equation Presented) A mixture of nitrate salt and chlorotrimethylsilane is found to be a mild and efficient reagent for the direct oxidative conversion of thiols (1) and disulfides (2) to the corresponding sulfonyl chlorides (3) in excellent yields through oxidative chlorination. Sulfides and sulfoxides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases these reactions are highly selective, simple, and clean, affording products in high yield and purity.
