Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)–C(sp3) Bond Cleavage and Functionalizations
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- 作者：Kunfang Jia ; Fuyuan Zhang ; Hanchu Huang ; Yiyun Chen
- 刊名：Journal of the American Chemical Society
- 出版年：2016
- 出版时间：February 10, 2016
- 年：2016
- 卷：138
- 期：5
- 页码：1514-1517
- 全文大小：389K
- ISSN：1520-5126
文摘
The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light-induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp3)–C(sp3) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.