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A photoredox-neutral radical-radical cross-coupling is described for the synthesis of 3-hydroxy-3-alkyloxindoles using isatins and benzyl carboxylic acids as substrates and 2,4,5,6-tetra(-carbazol-9-yl)isophthalonitrile (4CzIPN) as the photocatalyst. The method features a broad substrate scope and good functional group tolerance, providing 30 sterically hindered alcohols with moderate to excellent yields. This approach utilizes inexpensive and commercially available starting materials, avoiding the use of transition metals, extra oxidants/reductants, and harsh reaction conditions, showcasing significant applicability and environmental friendliness.
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http://dx.doi.org/10.1021/acs.joc.4c01268 | DOI Listing |
J Org Chem
August 2024
Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
A photoredox-neutral radical-radical cross-coupling is described for the synthesis of 3-hydroxy-3-alkyloxindoles using isatins and benzyl carboxylic acids as substrates and 2,4,5,6-tetra(-carbazol-9-yl)isophthalonitrile (4CzIPN) as the photocatalyst. The method features a broad substrate scope and good functional group tolerance, providing 30 sterically hindered alcohols with moderate to excellent yields. This approach utilizes inexpensive and commercially available starting materials, avoiding the use of transition metals, extra oxidants/reductants, and harsh reaction conditions, showcasing significant applicability and environmental friendliness.
View Article and Find Full Text PDFFront Chem
October 2022
Central Nervous System Drug Key Laboratory of Sichuan Province, Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou, China.
A metal- and aldehyde-free visible-light-driven photoredox-neutral alkene acylarylation with readily available cyanoarenes is described. A variety of 3-(arylmethyl)chroman-4-ones (i.e.
View Article and Find Full Text PDFChem Soc Rev
August 2017
Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Visible-light photoredox catalysis has been esteemed as one sustainable and attractive synthetic tool. In the past four years, a new yet challenging trend, visible-light-driven redox-neutral radical C-C cross-coupling involving putative radical intermediates, has been booming rapidly. Its advent brings a powerful platform to achieve non-classical C-C connections, and should lead to fundamental changes in retrosynthetic analysis.
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