Neutral Chalcogen Bonding Enabled Photoinduced Cross-Electrophile C—S/Se Coupling of Aryl Iodides via SRN1 Process

Yong-Liang Tu; Xiang Li; Bei-Bei Zhang; Gui-Ying Fu; Ling Zhou; Wei Gong; Xiang-Yu Chen

doi:10.1002/cjoc.202401197

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (11) :1299 -1305. DOI: 10.1002/cjoc.202401197

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Neutral Chalcogen Bonding Enabled Photoinduced Cross-Electrophile C—S/Se Coupling of Aryl Iodides via S_RN1 Process

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Abstract

Cross-coupling reactions between aryl halides and thiolates or selenolates typically require transition metals, photocatalysts, strong bases, or/and malodorous thiols/selenols, with various mechanisms proposed. This study aims to leverage a new application of neutral ChB to address these challenges and enable a very simple photoinduced cross-electrophile C—S/Se coupling using readily available chalcogen electrophiles. Mechanistic investigations have revealed the important role of neutral ChB in facilitating single electron transfer processes, thereby enabling the generation of thiolates/selenolates from stable chalcogen electrophiles and α-aminoalkyl radicals, which possess the capability to abstract halogen atoms from aryl iodides. Moreover, the study provided support for the radical nucleophilic substitution mechanism.

Keywords

Chalcogen bonding / Cross-electrophile coupling / Selenosulfonates / Organic halides / S_RN1 mechanism

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Yong-Liang Tu, Xiang Li, Bei-Bei Zhang, Gui-Ying Fu, Ling Zhou, Wei Gong, Xiang-Yu Chen. Neutral Chalcogen Bonding Enabled Photoinduced Cross-Electrophile C—S/Se Coupling of Aryl Iodides via S_RN1 Process. Chinese Journal of Chemistry, 2025, 43(11): 1299-1305 DOI:10.1002/cjoc.202401197