Abstract
AbstractThe development of a conjugation method initiated by irradiation of long-wavelength light (>500 nm) to prepare densely functionalized molecules while avoiding undesired photodegradation has attracted considerable attention. Here we show an amide bond formation method based on the photoreaction of 3-acylindolizines in the presence of amines triggered via red-light irradiation. Photooxidation of 3-acylindolizines using a catalytic amount of a photosensitizer and red light-emitting diodes (660 nm) affords the corresponding conjugated amides in nearly quantitative yields within <5 min. This transformation can be performed in aqueous organic solvents and is applicable to diverse aliphatic amines with various functional groups, including the moieties responsive to short-wavelength light.
Funder
MEXT | Japan Society for the Promotion of Science
Incentive Projects from RIKEN
Japan Agency for Medical Research and Development
the Cooperative Research Project of Research Center for Biomedical Engineering, from Tokyo Medical and Dental University Pioneering Project “Chemical Probe” from RIKEN
Publisher
Springer Science and Business Media LLC
Subject
Materials Chemistry,Biochemistry,Environmental Chemistry,General Chemistry
Cited by
1 articles.
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