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CeCl 3 ⋅7H 2 O‐NaI Promoted Regioselective Sulfenylation of Indoles with Sulfonylhydrazides
Author(s) -
Nookaraju U.,
Begari Eeshwaraiah,
Yetra Ravikiran Reddy,
Kumar Pradeep
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201500014
Subject(s) - regioselectivity , reagent , chemistry , sulfur , reactivity (psychology) , alkyl , aryl , functional group , combinatorial chemistry , alkoxy group , organic chemistry , medicinal chemistry , catalysis , medicine , alternative medicine , polymer , pathology
A simple and highly efficient method has been developed for the regioselective sulfenylation of a wide variety of indoles with alkyl and aryl sulfonylhydrazides as a sulphur source and CeCl 3 ⋅7H 2 O‐NaI as an inexpensive and readily available reagent system. This method involves the breaking of sulfur–oxygen and sulfur–nitrogen bonds and making of carbon‐sulfur bond. The method provides high yields of the products with enhanced regioselectivity. We studied the reactivity of various electron rich and electron deficient indoles towards the sulfenylation reaction. The indoles containing electron donating group reacts fast towards the sulfenylation reaction as compared to the indoles containing electron withdrawing groups. More over functional groups like alkoxy, aryloxy, bromo, nitro, cyano, ester, were well tolerated under the established reaction conditions. We also proposed a plausible mechanism for this transformation. The experimental simplicity and environmentally benign nature of the reagent system makes this method an attractive alternative to established methods.