Journal
ACS CATALYSIS
Volume 7, Issue 6, Pages 3818-3823Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00840
Keywords
C-H acylation; photocatalysis; dual catalysis; palladium catalysis; indoles; flow chemistry
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Funding
- University of Leuven
- Flanders Innovation & Entrepreneurship (VLAIO)
- COST (European Cooperation in Science and Technology) Action CH-Activation in Organic Synthesis [CA15106]
- Ministry of Education and Science of the Russian Federation [02.a03.0008]
- Dutch Science Foundation (NWO) via an ECHO grant [713.013.001]
- Dutch Science Foundation (NWO) via VIDI grant [14150]
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A mild and versatile protocol for the C-H acylation of indoles via dual photoredox/transition-metal catalysis was established in batch and flow. The C-H bond functionalization occurred selectively at the C-2 position of N-pyrimidylindoles. This room-temperature protocol tolerated a wide range of functional groups and allowed for the synthesis of a diverse set of acylated indoles. Various aromatic as well as aliphatic aldehydes (both primary and secondary) reacted successfully. Interestingly, significant acceleration (20 to 2 h) and higher yields were obtained under micro flow conditions.
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