70291-88-2

Upstream product

• 120-72-9 indole 
• 882-33-7 diphenyldisulfane 
• 54491-43-9 3-phenylthioindole 
• 5813-48-9 Methanesulfenyl chloride 
• 108-98-5 thiophenol 
• 14204-24-1 N-(phenylthio)succinimide 
• 3419-91-8 N-(2-pyridyl)indole 
• 80-17-1 benzenesufonyl hydrazide 
• 873-55-2 sodium benzenesulfonate 
• 931-59-9 benzenesulfenyl chloride 
• 200617-53-4 3,3-bis(phenylthio)-3H-indole 
• 63955-67-9 1-methyl-3-(phenylthio)-1H-indole 
• 136506-30-4 1-(2-phenylsulfonylethyl)-2,3-diphenylthioindole 
• 136506-29-1 1-(2-(phenylsulfonyl)ethyl)-1H-indole 

Downstream Products

• 98508-75-9 1-Benzyl-2,3-bis-phenylsulfonylindole 
• 98508-79-3 (2,3-Bis-benzenesulfonyl-indol-1-yl)-acetonitrile 
• 120517-31-9 5-chloro-2-(methylthio)-1H-indole 
• 63955-64-6 1-methyl-2,3-bis(phenylthio)-1H-indole 
• 51072-83-4 2-methyl-1H-indole-3-carbonitrile 
• 51072-85-6 2-phenyl-1H-indole-3-carbonitrile 
• 98508-76-0 2,3-Bis-benzenesulfonyl-1-ethyl-1H-indole 
• 108698-81-3 1-benzyl-2,3-bis(phenylthio)indole 

Relevant academic research and scientific papers

Cp*Co(iii)-catalyzed C2-thiolation and C2,C3-dithiolation of substituted indoles withN-(arylthio)succinimide

A general and efficient Cp*CoIII-catalyzed C2-thiolation and C2,C3-dithiolation of indole derivatives has been achieved employingN-(aryl/alkylthio)succinimide as a thiolating reagent. This external oxidant-free method utilizes only catalytic amounts of additive and tolerates various functional groups to afford various thiolated products in good yields. Control experiments revealed the importance of the Cp*CoIII-catalyst for both C2- and C3-thiolation.

Cu-catalysed direct bis-thiolation of benzoheterocycles with arylsulfonyl hydrazides

A series of bis-arylsulfenylated indoles (10), benzofurans (3), and benzothiophenes (3) and of monosulfenylated indoles (5), 12 of which are novel, were prepared in good yields via a Cu-catalysed direct sulfenylation of benzoheterocycles with arylsulfonyl hydrazides. Sulfonothioates are probably the major thiolated intermediates in this transformation.

Metal Free Mono- and 2,3-Bis-sulfenylation of Indoles in Water with Sodium Sulfinates as a Sulfur Source

An iodine-PPh3 mediated sulfenylation of indoles in water with stable and odorless sodium sulfinates as the sulfur source is described. The reaction could afford monosulfenylated indoles in moderate to excellent yields under metal free conditions. Moreover, double C—H sulfenylation of indoles at 2- and 3-positions has also been achieved by using excess sodium sulfinates under the optimized reaction conditions.

Iodine-Catalyzed Mono- and Disulfenylation of Indoles in PEG400 through a Facile Microwave-Assisted Process

An iodine-catalyzed versatile and green method for the synthesis of mono- and 2,3-disulfenylindoles was developed. Various indoles reacted with sodium alkyl- and arylsulfinates by using hydrogen peroxide as the oxidizing agent in PEG400 under microwave conditions. This simple method enabled the rapid synthesis of mono- and 2,3-disulfenylindoles in good to excellent yields under metal-free conditions. Furthermore, this protocol is environmentally friendly, odorless, and operationally easy and can be performed within short reaction times under mild reaction conditions with excellent functional-group tolerance.

Iodine-catalysed versatile sulfenylation of indoles with thiophenols: controllable synthesis of mono- and bis-arylthioindoles

A versatile method for the synthesis of mono- and bis-arylthioindoles via I2 catalysed direct oxidative sulfenylation of indoles with thiophenols (especially mercaptobenzoic acids) has been presented. This system features environmental friendliness, easy operation, and mild reaction conditions, and shows a broad functional group tolerance furnishing good to excellent yields.

Metal free sulfenylation and bis-sulfenylation of indoles: Persulfate mediated synthesis

A method which avoids metal and halogen for the synthesis of 3-arylthioindoles from indoles and diaryl disulfides using ammonium persulfate in methanol has been presented. Moreover, double C-H sulfenylation of indoles at 2 and 3-positions has also been ac

Efficient synthesis of 3-selanyl- and 3-sulfanylindoles employing trichloroisocyanuric acid and dichalcogenides

3-Arylselanyl- and 3-arylsulfanylindoles were prepared in EtOAc, by the reaction of indole with the diaryl dichalcogenide-trichloroisocyanuric acid (TCCA) reagent system. The products were efficiently and conveniently obtained, at room temperature and in

Mechanism of the second sulfenylation of indole

Sulfenylation of indole using a sulfenyl chloride occurs initially at the 3-position of the ring, leading to a 3-indolyl sulfide. When an excess of sulfenyl chloride is used, a second sulfide group is introduced at the 2-position, and an indolyl 2,3-bis-sulfide results. We have demonstrated that this second sulfenylation occurs not by direct introduction of the second sulfide at the 2-position but via initial formation of an indolenium 3,3-bis-sulfide intermediate, followed by migration of one of the sulfide groups to the 2-position. This was achieved by the isolation of two examples of 3H-indole 3,3-bis-sulfides and by subsequent demonstration that they rearrange to the indolyl 2,3-bis-sulfides by treatment with sulfenyl halides.

Regioselective synthesis of mixed indole 2,3-bis(sulfides). A study of the mechanism of the second sulfenylation of indole

Sulfenylation of indole using sulfenyl chlorides leads to the initial formation of a 3-indolyl sulfide, while excess reagent introduces a second sulfide at the 2-position of the ring. The mechanism of this second sulfenylation has not, to date, been rigor

Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction.We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring.In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched.Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides.This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.