A1 Journal article (refereed)
Halogen bonding and mechanochemistry combined : synthesis, characterization, and application of N-iodosaccharin pyridine complexes (2024)

Schumacher, C., Truong, K.-N., Ward, J. S., Puttreddy, R., Rajala, A., Lassila, E., Bolm, C., & Rissanen, K. (2024). Halogen bonding and mechanochemistry combined : synthesis, characterization, and application of N-iodosaccharin pyridine complexes. Organic Chemistry Frontiers, 11(3), 781-795. https://doi.org/10.1039/D3QO01512B

JYU authors or editors

Publication details

All authors or editors: Schumacher, Christian; Truong, Khai-Nghi; Ward, Jas S.; Puttreddy, Rakesh; Rajala, Anssi; Lassila, Elias; Bolm, Carsten; Rissanen, Kari

Journal or series: Organic Chemistry Frontiers

ISSN: 2052-4110

eISSN: 2052-4129

Publication year: 2024

Publication date: 05/12/2023

Volume: 11

Issue number: 3

Pages range: 781-795

Publisher: Royal Society of Chemistry (RSC)

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/D3QO01512B

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/93018

Web address of parallel published publication (pre-print): https://chemrxiv.org/engage/chemrxiv/article-details/6503f9e299918fe537fb3966

Abstract

Halogen-bonded complexes are utilized across a myriad of synthetic chemistry fields, with halogen(I) complexes such as Barluenga's reagent being ubiquitous in halogenation reactions. The preparation of Barluenga's reagent requires the use of heavy metal salts and vast amounts of chlorinated solvents. In line with a more modern, environmentally conscious ethos, halogen-bonded adducts and a halogen(I) complex similar to Barluenga's reagent based on N-iodosaccharin were prepared by mechanochemical processes for the first time. The general absence of solvents or the use of vanishingly small amounts of ethyl acetate in a liquid-assisted grinding approach during mechanochemical preparations enabled the homoleptic [(DMAP)–I–(DMAP)]+ iodine(I) complex to be synthesized. The as prepared mechanochemical materials were used in the iodination of antipyrine, demonstrating their potential use as surrogates for Barluenga's reagent in both solution and solid-state syntheses.

Keywords: coordination complexes; halogens; chemical bonds

Contributing organizations

Related projects

Ministry reporting: Yes

VIRTA submission year: 2023

JUFO rating: 1