Solvent based selectivity in the synthesis of di(2-aryl-1H-3-indolyl) sulfides and 1-aryl-2-[(2-aryl-1H-3-indolyl)sulfanyl]-1-ethanones

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

“…Manishankar and co-workers dealt with a facile Fischer indole process to convert thiodiketones 97 to bis(indol-3-yl)sulfides 98 by refluxing them with phenylhydrazine hydrochloride salt in ethanol [ 81 ]. Interestingly, changing the solvent to THF switched the product to thioketone 99 ( Scheme 14 ).…”

TFA/DMSO‐Promoted Cross‐Dehydrogenative Coupling of Hetaryl Thiols with Indoles: Access to 3‐(Hetarylsulfenyl)indole under Mild Conditions

“…(1) construction of the indole ring of 3‐sulfenylindole derivatives could be constructed by cyclization reactions of phenylhydrazine hydrochloride, [10] 2‐alkynylanilines, [11] N,N ‐Dialkyl‐2‐iodoanilines via one‐pot reaction, [12] and 2‐( gem dibromo(chloro)vinyl)anilines; [13] and (2) sulfenylation [14] of pre‐existing indole rings using an array of electrophilic sulfenylating agents such as disulfides, [15] sulfonyl chlorides, [16] N ‐(arylthio)phthalimides, [17] N ‐(arylthio)succinimides/Cp*Co(III), [18] sulfinic acid derivatives (acids [19] /esters [20] /sodium salts [21] ), sulfonyl hydrazides, [22] aryl halides/thiourea/CuI, [23] arylboronic acids/S 8 , [24] Bunte salts [25] and 1‐aryltriazene/CS 2 [26] . It should be noted that some electrophilic sulfenylating agents are moisture‐ and air‐ sensitive, difficult to prepare and not readily commercially available.…”

Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles

“…There are many efficient methodologies for the synthesis of sulfenylindoles reported in the literature [ 20 , 21 , 22 , 23 , 24 , 25 ]. Among them, the direct sulfenylation of indoles is one of the most efficient and common strategies [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ].…”