20335-69-7

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 25, p. 1732, 1977 DOI: 10.1248/cpb.25.1732

InChI:InChI=1/C16H17NO2S/c1-13-6-8-16(9-7-13)20(18,19)17-11-10-14-4-2-3-5-15(14)12-17/h2-9H,10-12H2,1H3

Upstream product

• 66895-91-8 N-(2-phenylethyl)-N-[(4-methylphenyl)sulfonyl]glycine 
• 38256-56-3 1-(2-bromo-ethyl)-2-bromomethyl-benzene 
• 70-55-3 toluene-4-sulfonamide 
• 50-00-0 formaldehyd 
• 5450-75-9 4-methyl-N-(2-phenylethyl)benzenesulfonamide 
• 159421-27-9 N-(3-butynyl)-4-methyl-N-(2-propynyl)benzenosulfonamide 
• 74-86-2 acetylene 
• 195608-42-5 1-(4-methylphenylsulfonyl)-1-azacyclodec-5-ene-3,7-diyne 
• 86119-84-8 phosphoric acid 
• 7719-09-7 thionyl chloride 
• 187887-01-0 N-(3-hydroxypropyl)-4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 152453-96-8 N-(2-formylethyl)-N-(3-propynyl)-p-toluenesulfonamide 
• 5720-05-8 4-methylphenylboronic acid 
• 195987-27-0 1,2,3,4-tetrahydroisoquinoline-2-sulfonyl chloride 

Downstream Products

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

S(vi) in three-component sulfonamide synthesis: Use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling

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Synthesis of tetrahydroisoquinolines through TiCl4-mediated cyclization and Et3SiH reduction

A versatile and efficient telescoped reaction sequence for the synthesis of tetrahydroisoquinolines (THIQs) is reported that uses TiCl4 to promote cyclization of a benzylaminoacetal derivative and Et3SiH for reduction of the intermediate 4-hydroxy-THIQ. This method is complimentary to the classical Pomeranz-Fritsch and related reactions since it tolerates electron-withdrawing substituents and allows access to 8-substituted THIQs.

Visible light mediated oxidation of benzylic sp3 C-H bonds using catalytic 1,4-hydroquinone, or its biorenewable glucoside, arbutin, as a pre-oxidant

Benzylic ethers undergo a visible light induced C-H activation and oxygen insertion to give the corresponding benzoate esters in moderate to good yields. The conditions employ substoichiometric amounts of 1,4-hydroquinone with copper(ii) chloride dihydrate as an electron-transfer mediator, oxygen as the terminal oxidant and dimethyl carbonate as solvent under visible light irradiation. The naturally occurring glucoside, arbutin, which is commercially available or can be accessed via extraction of the leaves of bearberry (Arctostaphylos uva-ursi) or elephant ears (Bergenia crassifolia) can be used as a biorenewable source of 1,4-hydroquinone. The methodology exploits the increase in oxidizing ability of quinones upon irradiation with visible light, and offers a sustainable alternative for the late stage oxidative functionalization of benzylic C-H bonds. It is applicable to a range of cyclic benzylic ethers such as isochromans and phthalans, and simple benzyl alkyl ethers. It can also be applied in the oxidation of benzylic amines into amides, and of diarylmethanes into the corresponding ketones. Mechanistic studies suggest that the reaction proceeds by H-abstraction by the photo-excited triplet benzoquinone to give a benzylic radical that subsequently reacts with molecular oxygen.

Copper-Catalyzed Transsulfinamidation of Sulfinamides as a Key Step in the Preparation of Sulfonamides and Sulfonimidamides

Secondary or tertiary sulfinamides are prepared by copper-catalyzed transsulfinamidation of primary sulfinamides with O-benzoyl hydroxylamines. Subsequent oxidations of the resulting products lead to the corresponding sulfonamides. Treatment of N-aryl sulfinamides with O-benzoyl hydroxylamines under copper catalysis provides N-aryl sulfonimidamides.

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A copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-chloroamines is described. This coupling reaction provides an efficient and simple approach to a wide range of sulfonamides in moderate to good yields under mild conditions. Mechanistic investigation suggests that a radical process and transition-metal catalysis are merged in this tandem reaction.

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DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents

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A novel organic electron donor derived from N-methylisatin

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