Metal-free, room temperature, acid-K2S2O8 mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins

Srinivas Ambala; Rohit Singh; Maninder Singh; Pankaj Singh Cham; Ria Gupta; Gurunadham Munagala; Kushalava Reddy Yempalla; Ram A. Vishwakarma; Parvinder Pal Singh

doi:10.1039/C9RA06414A

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Metal-free, room temperature, acid-K₂S₂O₈ mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins†

Srinivas Ambala,‡^ab Rohit Singh,‡^ab Maninder Singh,^a Pankaj Singh Cham,^a Ria Gupta,^ab Gurunadham Munagala,^ab Kushalava Reddy Yempalla,^ab Ram A. Vishwakarma^ab and Parvinder Pal Singh*^ab

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* Corresponding authors

^a Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, India
E-mail: ppsingh@iiim.ac.in

^b Academy of Scientific and Innovative Research, India

Abstract

Here, we have developed a simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (K₂S₂O₈) under an open atmosphere. Styrenes and mono-substituted olefins give stereo-selective corresponding E-nitroolefins under optimized conditions, however, 1,1-bisubstituted olefins give a mixture of E- and Z-nitroolefins. The optimized conditions work well with electron-donating, electron-withdrawing, un-substituted and heterocyclic styrenes and mono-substituted olefins and give corresponding nitroolefins with good to excellent yields.

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Article information

DOI: https://doi.org/10.1039/C9RA06414A
Article type: Paper
Submitted: 16 Aug 2019
Accepted: 05 Sep 2019
First published: 25 Sep 2019
This article is Open Access

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RSC Adv., 2019,9, 30428-30431

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Metal-free, room temperature, acid-K₂S₂O₈ mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins

S. Ambala, R. Singh, M. Singh, P. S. Cham, R. Gupta, G. Munagala, K. R. Yempalla, R. A. Vishwakarma and P. P. Singh, RSC Adv., 2019, 9, 30428 DOI: 10.1039/C9RA06414A

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