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Synlett 2019; 30(18): 2015-2021
DOI: 10.1055/s-0039-1690498
DOI: 10.1055/s-0039-1690498
synpacts
Emerging Catalyst Control in Cobalt-Catalyzed Oxidative Hydrofunctionalization Reactions
This work was supported by the ‘Thousand Talents Plan’ Youth Program, and startup fund from College of Chemistry and Molecular Engineering, Peking University and BNLMS.Further Information
Publication History
Received: 18 June 2019
Accepted after revision: 09 July 2019
Publication Date:
25 July 2019 (online)
Abstract
Oxidative functionalization has emerged as an important pathway in Co-catalyzed hydrogen atom transfer (HAT) hydrofunctionalization reactions. Notably, evidence was found for the participation of organometallic intermediates in such radical-polar crossover processes. These findings provide opportunities for catalyst control that was previously absent in HAT catalysis. In this article, we summarize the recent progress towards this direction involving carbon–heteroatom bond-forming intra- and intermolecular reactions, including work from our own group.
1 Introduction
2 Oxidative Trapping by Solvents and Intramolecular Nucleophiles
3 Intermolecular Oxidative Hydrofunctionalization
4 Conclusion and Outlook
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For representative recent examples of related processes:
For representative examples of metal-complexed radicalophiles:
Selected examples:
Selected examples:
For a related radical hydrofluorination reaction:
Compound 31, 1-hydroxy-1,2-benziodoxol-3(1H)-one (or iodosobenzoic acid, IBA) is a well-known group-transferring oxidant:
For an example of early use: