打断 Barton-McCombie 反应：- 烷基硫代碳酸酯的水相脱氧三氟甲基化反应。
Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of -Alkyl Thiocarbonates.
机构信息
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States.
出版信息
Org Lett. 2021 Feb 5;23(3):808-813. doi: 10.1021/acs.orglett.0c04039. Epub 2021 Jan 14.
Abstract
The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of -alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.
摘要
脂肪族体系的位点选择性三氟甲基化仍然是一个重要的挑战。本工作描述了一种光驱动、铜介导的-烷基硫代碳酸酯的三氟甲基化反应。该反应具有广泛的官能团容忍性（例如，炔烃、烯烃、苯酚、游离醇、富电子和缺电子芳基），因此为三氟甲基化提供了正交性和实用性。提出了一种自由基有机金属反应机制。
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