Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride

Laura D'Andrea; Simon Jademyr

doi:10.3762/bjoc.21.4

Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride

Beilstein J Org Chem. 2025 Jan 7:21:39-46. doi: 10.3762/bjoc.21.4. eCollection 2025.

Authors

Laura D'Andrea^{1

2}, Simon Jademyr^{1

3}

Affiliations

¹ Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 København Ø, Denmark.
² current address: Department of Chemistry and Bioscience, Aalborg University, Fredrik Bajers Vej 7H, 9220 Aalborg, Denmark.
³ current address: Centre for Analysis and Synthesis, Lund University, Naturvetarvägen 14, 223 62 Lund, Sweden.

Abstract

Phenethylamines and phenylisopropylamines of scientific relevance can be prepared with a NaBH₄/CuCl₂ system in 10 to 30 minutes via reduction of substituted β-nitrostyrenes. This one-pot procedure allows the quick isolation of substituted β-nitrostyrene scaffolds with 62-83% yield under mild conditions, without the need for special precautions, inert atmosphere, and time-consuming purification techniques.

Keywords: 2C-X; CuCl2; NaBH4; phenethylamine; β-nitrostyrene.

Grants and funding

L.D’A. acknowledges the EU Horizon 2020, Innovative Training Network SAFER (765657).