Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 20, Pages 11211-11216Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202101104
Keywords
[2+2]; retro-Mannich-type cycloaddition; amine radical cation; cyclohepta[b]indole; photoredox catalysis
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Funding
- National Key RAMP
- D Program of China [2018YFC0310905]
- National Science Foundation of China [21632002, 21871012]
- Guangdong Provincial Key RD Program [2020B0303070002]
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A novel method for the synthesis of cyclohepta[b]indoles in high yields was developed through a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones. Experimental and computational studies indicated that the reaction is initiated by single-electron oxidation of an enaminone moiety, leading to cyclobutane formation and rapid fragmentation in a radical-cation state to produce cyclohepta[b]indoles.
A novel method for the concise synthesis of cyclohepta[b]indoles in high yields was developed. The method involves a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones. Experimental and computational studies suggested that the reaction is a photoredox process initiated by single-electron oxidation of an enaminone moiety, which undergoes subsequent cyclobutane formation and rapidly fragmentation in a radical-cation state to form cyclohepta[b]indoles.
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