期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 4, 页码 1735-1741出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912214
关键词
aldehydes; C-H activation; green chemistry; olefins; photochemistry
资金
- Latsis Foundation through the program EPISTHMONIKES MELETES 2015 (PhotoOrganocatalysis: Development of new environmentally-friendly methods for the synthesis of compounds for the pharmaceutical and chemical industry)
- State Scholarships Foundation (IKY) through a PhD fellowship through the Strengthening of Human Resources through Doctoral Research program of the Operational Program Human Resource Development, Education and Lifelong Learning 2014-2020
- European Union (European Social Fund ESF)
- Greek national funds
- COST Action C-H Activation in Organic Synthesis (CHAOS) [CA15106]
Direct alkylation of C(sp(2))-H bonds to convert an aldehyde into a ketone is a notorious transformation, due to the laborious challenge of the formation of ketyl or acyl radicals. Herein, we report a green, cheap, metal-free and efficient method for the hydroacylation of olefins in water. This photochemical protocol utilizes phenylglyoxylic acid, a commercially available small organic molecule, as the photoinitiator, water as the solvent and household fluorescent lamps as the irradiation source, leading to a broad substrate scope of products in moderate to good yields. A wide range of aromatic and aliphatic aldehydes, terminal and non-terminal alkenes and pharmaceutically relevant molecules can be employed, without the need of directing groups and additives or metal catalysts.
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