4.5 Review

Recent Advances in Minisci-type Reactions and Applications in Organic Synthesis

Journal

CURRENT ORGANIC CHEMISTRY
Volume 25, Issue 8, Pages 894-934

Publisher

BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1385272824999201230211157

Keywords

Minisci-type reaction; radicals' generation; C-H functionalization heterocycles; transition metal-promoted/catalyzed Minisci reactions; light-mediated Minisci reactions; transition metal-free Minisci reactions

Funding

  1. National Natural Science Foundation of China [31972850]
  2. Shandong Key Research Program [2019GSF108223]
  3. open funds of the State Key Laboratory of Fluorinated functional membrane materials [YJY2020001]
  4. open funds of the State Key Laboratory of Microbial Technology Open Projects Fund [M2020-05]

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Minisci-type reactions involve the addition of carbon-centered radicals to basic heteroarenes followed by formal hydrogen atom loss. New radical generation strategies have expanded the variety of radical precursors that can be used, often operating under milder conditions. Radial generation methods based on photoredox catalysis and electrochemistry are popular approaches that are now available for synthetic chemists.
Minisci-type reactions have been widely known as reactions that involve the addition of carbon-centered radicals to basic heteroarenes followed by formal hydrogen atom loss. While the originally developed protocols for radical generation remain in active use today, in recent years, the new array of radical generation strategies have allowed the use of a wider variety of radical precursors that often operate under milder and more benign conditions. New transformations based on free radical reactivity are now available to a synthetic chemist, to utilize a Minisci-type reaction. Radical-generation methods based on photoredox catalysis and electrochemistry, which utilize thermal cleavage or the in situ generation of reactive radical precursors, have become popular approaches. Our review will cover the remarkable literature that has been reported on this topic in recent 5 years, from 2015-01 to 2020-01, in an attempt to provide guidance to the synthetic chemist on both the challenges that need to be overcome and the applications in organic synthesis.

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