Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 24, Pages 15077-15086Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02355
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Funding
- sao Paulo Research Foundation FAPESP [2018/00106-7, 2015/21110-4, 2013/07276-1, 2016/21993-6, 2016/24020-9]
- CNPq - National Council of Science and Technology, Brazil
- CAPES - Ministry of Education
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [16/24020-9, 15/21110-4] Funding Source: FAPESP
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We have investigated both batch and continuous flow photoarylations of enol-acetates to yield different alpha-arylated aldehyde and ketone building blocks by using diazonium salts as the aryl-radical source. Different porphyrins were used as SET photocatalysts, and photophysical as well as electrochemical studies were performed to rationalize the photoredox properties and suggest mechanistic insights. Notably, the most electron-deficient porphyrin (meso-tetra-(pentafluorophenyl)porphyrin) shows the best photoactivity as an electron donor in the triplet excited state, which was rationalized by the redox potentials of excited states and the turnover of the porphyrins in the photocatalytic cycle. A two-step continuous protocol and multigram-scale reactions are also presented revealing a robust, cost-competitive, and easy methodology, highlighting the significant potential of porphyrins as SET photocatalysts.
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