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Oxy-sulfonylation of terminal alkynesviaC-S coupling enabled by copper photoredox catalysis
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Oxy-sulfonylation of terminal alkynesviaC-S coupling enabled by copper photoredox catalysis

V.K.K. Pampana, Vaibhav Pramod Charpe, Arunachalam Sagadevan, Deb Kumar Das, Chun-Cheng Lin, Jih Ru HwuKuo Chu Hwang
Green Chemistry, 卷.23(10), 頁碼.3569-3574
05/2021

摘要

Environmental Chemistry Pollution
We report the first literature example using visible light-induced trimethylsilyl azide (TMS-N 3 )-assisted copper-catalyzed oxy-sulfonylation of terminal C-C bonds to form β-keto sulfones (C-S bond formation). TMS-N 3 promotes the reaction by facilitating the formation of sulfonyl radicals, which later decompose into N 2 gas upon light irradiation. This method involves the use of commercially available and stable starting materials. Also, a wide range of functional groups have been well-tolerated under the current photoredox process, evading the side product formation. Potent biologically active compounds, such as CES1, 11β-HSD1 inhibitors, anti-analgesic agents, and reactive synthesis intermediates were synthesized to demonstrate the synthetic utility of the current methodology. Moreover, green chemistry metrics and Eco-scale evaluation for the current photochemical method show that the protocol is eco-friendly and highly efficient.

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