Experimental and theoretical investigations of regioselective functionalization of 3-hydroxy bisindoles with thiols
Literature Information
Publication Date
2018-11-05
DOI
10.1039/C8OB02118J
Impact Factor
3.876
Authors
Nitika Sharma, Rama Krishna Peddinti
View Original
Abstract
An instant and efficient p-TSA·H2O-catalyzed sulfenylation reaction of 3-hydroxy bisindole derivatives is reported. This highly regioselective approach afforded C-3 functionalized products in excellent yield, and this methodology was found to be compatible with both aromatic and aliphatic thiols having electronic and steric divergence as well as diverse functional groups. The sulfenylation reaction was performed at room temperature with a green solvent with minimal catalyst loading and proceeded with the involvement of a quasi-antiaromatic-2H-indol-2-one ring intermediate. Moreover, the experimental results obtained for the sulfenylation reaction of 3-hydroxy bisindoles were supported by theoretical calculations in order to comprehend the regioselectivity and chemical reactivity observed in the thiolation reaction of 3-hydroxy bisindoles. The protocol involved the SN1 pathway, as also demonstrated by theoretical calculations.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
(3beta,22E)-Stigmasta-5,22-dien-3-yl beta-D-glucopyranoside
CAS Number:
19716-26-8
Molecular Formula:
C35H58O6
![4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride structure](https://static.chemtradehub.com/structs/797/79793-00-3-de16.webp "4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride structure")
4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride
CAS Number:
79793-00-3
Molecular Formula:
C8H8Cl4O2SSi
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