Visible-Light-Driven Photocatalytic Utilization of Sulfur Hexafluoride (SF <sub>6</sub> ) as an SF <sub>5</sub> Radical Source

Sulfur hexafluoride (SF6) is a potent greenhouse gas widely used in industry, but its chemical inertness has limited its use as a source of pentafluorosulfanyl (SF5) groups. We report herein a visible-light-driven photocatalytic transformation that enables SF6 to function as an SF5 radical source for the synthesis of SF5 enamides under ambient pressure. Using ynamides as radical acceptors, a range of β-SF5-substituted enamides were obtained under mild conditions in moderate to good yields. Mechanistic studies support the involvement of SF5 radical intermediates and a hydrogen atom transfer process rather than a radical chain pathway. The resulting SF5 enamides could be further transformed into diverse functionalized products, demonstrating their synthetic utility. This work highlights the potential of SF6 as a practical SF5 radical source for constructing valuable SF5-containing organic molecules under photocatalytic conditions. This work provides a new strategy for the direct utilization of SF6 in synthetic organic chemistry.

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Journal
Organic Letters
Published
2026-05-23
DOI
https://doi.org/10.1021/acs.orglett.6c01795
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Visible-Light-Driven Photocatalytic Utilization of Sulfur Hexafluoride (SF 6 ) as an SF 5 Radical Source

Tatsuhiro Uchikura, Takahiko Akiyama, Minami Tanaka
Organic Letters
Fluorine in Organic Chemistry
article

Visible-Light-Driven Photocatalytic Utilization of Sulfur Hexafluoride (SF 6 ) as an SF 5 Radical Source

Tatsuhiro Uchikura, Takahiko Akiyama, Minami Tanaka
article en

Abstract

Sulfur hexafluoride (SF6) is a potent greenhouse gas widely used in industry, but its chemical inertness has limited its use as a source of pentafluorosulfanyl (SF5) groups. We report herein a visible-light-driven photocatalytic transformation that enables SF6 to function as an SF5 radical source for the synthesis of SF5 enamides under ambient pressure. Using ynamides as radical acceptors, a range of β-SF5-substituted enamides were obtained under mild conditions in moderate to good yields. Mechanistic studies support the involvement of SF5 radical intermediates and a hydrogen atom transfer process rather than a radical chain pathway. The resulting SF5 enamides could be further transformed into diverse functionalized products, demonstrating their synthetic utility. This work highlights the potential of SF6 as a practical SF5 radical source for constructing valuable SF5-containing organic molecules under photocatalytic conditions. This work provides a new strategy for the direct utilization of SF6 in synthetic organic chemistry.

Organic Letters
Gakushuin University (JP)
Japan Society for the Promotion of Science
Industry, innovation and infrastructure
Openalex Percentile: Top 7%
Fluorine in Organic Chemistry
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Visible-Light-Driven Photocatalytic Utilization of Sulfur Hexafluoride (SF <sub>6</sub> ) as an SF <sub>5</sub> Radical Source — Tatsuhiro Uchikura, Takahiko Akiyama, et al. · Organic Letters (2026) | TGRS Research Map | TGRS