63955-64-6Relevant articles and documents
Metal Free Mono- and 2,3-Bis-sulfenylation of Indoles in Water with Sodium Sulfinates as a Sulfur Source
Liu, Changqing,Fan, Jian,Wu, Manyi,Chen, Jiahui,Zhao, Yiming,Xie, Meihua
, p. 819 - 825 (2018/07/30)
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.
Acid-catalyzed Isomerization of 3-Indolyl Sulfides to 2-Indolyl Sulfides: First Synthesis of 3-Unsubstituted 2-(Arylthio)indoles. Evidence for a Complex intermolecular Process
Hamel, Pierre,Girard, Yves,Atkinson, Joseph G.
, p. 2694 - 2699 (2007/10/02)
The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds.When catalyzed by trifluoracetic acid, the isomerisation proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction if these species to yield the rearranged isomer 4.A mechanism is proposed involving a role for the acid tn the sulfenyl-transfer steps.This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.