One-pot C-C, C-N, and C-S bond construction for synthesis of 3-sulfenylindoles directly from unactivated anilines involving dual palladium catalysis and mechanistic insights from DFT

Sumit K Rastogi; Richa Singh; Santosh Kumar; Abhishek Kumar Mishra; Mini Bharati Ahirwar; Milind M Deshmukh; Arun K Sinha; Ravindra Kumar

doi:10.1039/d2ob01606k

One-pot C-C, C-N, and C-S bond construction for synthesis of 3-sulfenylindoles directly from unactivated anilines involving dual palladium catalysis and mechanistic insights from DFT

Org Biomol Chem. 2023 Jan 25;21(4):838-845. doi: 10.1039/d2ob01606k.

Authors

Sumit K Rastogi^{1

2}, Richa Singh^{1

3}, Santosh Kumar^{1

2}, Abhishek Kumar Mishra¹, Mini Bharati Ahirwar⁴, Milind M Deshmukh⁴, Arun K Sinha^{1

2

5}, Ravindra Kumar^{1

2}

Affiliations

¹ Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow-226031, UP, India. ravindra.kumar1@cdri.res.in.
² Academy of Scientific & Innovative Research (AcSIR), Ghaziabad, UP-201002, India.
³ Department of Chemistry, Gaya College, Gaya, Bihar-823001, India.
⁴ Department of Chemistry, Dr Harisingh Gour Vishwavidyalaya (A Central University), Sagar, India.
⁵ Ranchi University, Ranchi, Jharkhand-834001, India.

PMID: 36602157
DOI: 10.1039/d2ob01606k

Abstract

An efficient dual Pd-catalytic system was developed for one-pot synthesis of 3-sulfenylindoles via C-C, C-N and C-S bond construction directly from unactivated 2-iodo(NH)anilines under mild reaction conditions. Furthermore, 3-selenyl/halo/carbon-functionalized indoles were synthesized in good yields and a short reaction time. The synthetic utility of 3-sulfenylindole was also demonstrated. The key role of solvent in palladium catalysis was unravelled by DFT.