A Mechanistic Investigation of the Visible-Light Photocatalytic Trifluoromethylation of Heterocycles Using CF3I in Flow
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- 作者：Dr. Yuanhai Su ; Koen P. L. Kuijpers ; Niels Kö ; nig ; Minjing Shang ; Prof. Dr. Volker Hessel and Dr. Timothy Noë ; l
- 刊名：Chemistry - A European Journal
- 出版年：2016
- 出版时间：August 22, 2016
- 年：2016
- 卷：22
- 期：35
- 页码：12295-12300
- 全文大小：973K
- ISSN：1521-3765
文摘
Photocatalytic radical trifluoromethylation strategies have impacted the synthesis of trifluoromethyl-containing molecules. However, mechanistic aspects concerning such transformations remain poorly understood. Here, we describe in detail the mechanism of the visible-light photocatalytic trifluoromethylation of N-methylpyrrole with gaseous CF3I in flow. The use of continuous-flow microreactor technology allowed for the determination of different important parameters with high precision (e.g., photon flux, quantum yield, reaction rate constants) and for the handling of CF3I in a convenient manner. Our data indicates that the reaction occurs through a reductive quenching mechanism and that there is no radical chain process present.