A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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-tekijät tai -toimittajat

Schumacher, Christian
Truong, Khai-Nghi
Ward, James
Puttreddy, Rakesh
Rissanen, Kari

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Schumacher, Christian; Truong, Khai-Nghi; Ward, Jas S.; Puttreddy, Rakesh; Rajala, Anssi; Lassila, Elias; Bolm, Carsten; Rissanen, Kari

Lehti tai sarja: Organic Chemistry Frontiers

ISSN: 2052-4110

eISSN: 2052-4129

Julkaisuvuosi: 2024

Ilmestymispäivä: 05.12.2023

Volyymi: 11

Lehden numero: 3

Artikkelin sivunumerot: 781-795

Kustantaja: Royal Society of Chemistry (RSC)

Julkaisumaa: Britannia

Julkaisun kieli: englanti

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

Julkaisun avoin saatavuus: Avoimesti saatavilla

Julkaisukanavan avoin saatavuus: Osittain avoin julkaisukanava

Julkaisu on rinnakkaistallennettu (JYX): https://jyx.jyu.fi/handle/123456789/93018

Rinnakkaistallenteen verkko-osoite (pre-print): https://chemrxiv.org/engage/chemrxiv/article-details/6503f9e299918fe537fb3966

Tiivistelmä

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.

YSO-asiasanat: kompleksiyhdisteet; halogeenit; kemialliset sidokset

Tieteenalat: