Sulfur‐ and Amine‐ Promoted Multielectron Autoredox Transformation of Nitromethane: Multicomponent Access to Thiourea Derivatives

Author:

Phaenok Supasorn12,Nguyen Le Anh34ORCID,Soorukram Darunee2,Nguyen Thi Thanh Tam5,Retailleau Pascal1,Nguyen Thanh Binh1

Affiliation:

1. Institut de Chimie des Substances Naturelles CNRS UPR 2301 Université Paris-Sud Université Paris-Saclay 1, av de la Terrasse 91198 Gif-sur-Yvette France

2. Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC) Faculty of Science Mahidol University Rama VI Road Bangkok 10400 Thailand

3. Graduate University of Science and Technology Vietnam Academy of Science and Technology 18 Hoang Quoc Viet, Cau Giay Hanoi Vietnam

4. Institute of Chemistry Vietnam Academy of Science and Technology 18 Hoang Quoc Viet, Cau Giay Hanoi Vietnam

5. Univ Paris Est Creteil CNRS Institut de Chimie et des Matériaux Paris-Est UMR 7182 2 rue Henri Dunant 94320 Thiais France

Abstract

AbstractThiourea derivatives are in‐demand motifs in organic synthesis, medicinal chemistry and material science, yet redox methods for the synthesis that start from safe, simple, inexpensive and readily available feedstocks are scarce. In this article, we disclose the synthesis of these motifs using elemental sulfur and nitromethane as the starting materials. The method harnesses the multi‐electron auto‐redox property of nitromethane in the presence of sulfur and amines, delivering thiourea products without any added oxidant or reductant. Extension of this reaction to cyclizable amines and/or higher homologues of nitromethane led to a wide range of nitrogen heterocycles and thioamides. Operationally simple, the reactions are scalable, tolerate a wide range of functional groups, and can be employed for the direct functionalization of natural products. Mechanistically, the nitro group was found to act as an oxidant leaving group, being reduced to ammonia whereas sulfur, along with the role of a sulfur building block for the thiocarbonyl group, behaved as a complementary reductant, being oxidized to sulfate.

Funder

Vietnam Academy of Science and Technology

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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