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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Porphyrins as Photoredox Catalysts in Csp(2)-H Arylations: Batch and Continuous Flow Approaches

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Author(s):
de Souza, Aline A. N. [1] ; Silva, Nathalia S. [1] ; Mueller, Andressa V. [2] ; Polo, Andre S. [2] ; Brocksom, Timothy J. [2, 1] ; de Oliveira, Kleber T. [1]
Total Authors: 6
Affiliation:
[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210580 Santo Andre, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: Journal of Organic Chemistry; v. 83, n. 24, p. 15077-15086, DEC 21 2018.
Web of Science Citations: 5
Abstract

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. (AU)

FAPESP's process: 15/21110-4 - Exploiting photocatalyzed reactions under continuous flow conditions by using porphyrinoid systems: (C-FlowPhotoChem)
Grantee:Kleber Thiago de Oliveira
Support type: Regular Research Grants
FAPESP's process: 18/00106-7 - Photocatalyzed reactions by using porphyrins and continuous flow conditions: arylations of heterocycles and activated olefins
Grantee:Kleber Thiago de Oliveira
Support type: Regular Research Grants
FAPESP's process: 16/24020-9 - Evaluation of processes photoassisted by Ru(II) and Re(I) polypyridyl compounds
Grantee:Andressa Vidal Muller
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 13/07276-1 - CEPOF - Optics and Photonic Research Center
Grantee:Vanderlei Salvador Bagnato
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 16/21993-6 - Evaluation of Ru(II) and Re(I) polypyridyl compounds on photoactive devices
Grantee:André Sarto Polo
Support type: Regular Research Grants