Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 25, Pages 8577-8580Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902473
Keywords
aryl cyclopropane; late-stage modification; photochemistry; radical chain reactions; beta-chloro ketones
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Funding
- German Science Foundation (DFG) [GRK 1626, KO 1537/18-1]
- Swedish Research Council [2014-04673, 2018-04589]
- Knut and Alice Wallenberg foundation [KAW2013.0031]
- Gcran Gustafsson foundation
- Kempe Foundation [SMK-1755]
- Swedish Foundation for Strategic Research [SB12-0070]
- Michael J. Fox foundation
- Swedish Research Council [2014-04673, 2018-04589] Funding Source: Swedish Research Council
- Swedish Foundation for Strategic Research (SSF) [SB12-0070] Funding Source: Swedish Foundation for Strategic Research (SSF)
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We report the visible-light-mediated synthesis of beta-chloro ketones from aryl cyclopropanes, oxygen, hydrochloric acid, and nitric acid. The operationally simple and catalyst-free method uses cheap standard laboratory reagents and displays broad functional-group tolerance. Moreover, scale up of the reaction and late-stage functionalization of bioactive compounds is possible, providing the opportunity to utilize the cyclopropane ring as a masked beta-chloro ketone in a reaction sequence. We propose a light-driven radical chain reaction initiated by the reaction of diluted hydrochloric and nitric acid to produce small quantities of molecular chlorine. The mechanistic hypothesis is supported by O-18 labelling and UV/Vis experiments, cyclovoltammetry, and several control reactions.
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