Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers

Title
Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers
Author(s)
조대원윤웅찬[윤웅찬]Patrick S. Mariano[Patrick S. Mariano]
Keywords
N-PHTHALOYL DERIVATIVES; POLYDONOR-SUBSTITUTED PHTHALIMIDES; TRANSFER-INITIATED PHOTOADDITION; PHOTOEXCITED-STATE RESPONSE; ELECTROCHEMICAL OXIDATION; ORGANOSILICON COMPOUNDS; PHOTOCYCLIZATION REACTIONS; MODEL SYSTEMS; PHOTOCHEMICAL STRATEGY; MACROBICYCLIC LIGAND
Issue Date
201402
Publisher
BEILSTEIN-INSTITUT
Citation
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, v.10, pp.514 - 527
Abstract
In this review, we describe direct and indirect photochemical approaches that have been developed for the preparation of phthalimide- and naphthalimide-based, lariat-type crown ethers. The direct route utilizes a strategy in which nitrogen-linked side chains containing polyethoxy-tethered phthalimides and naphthalimides, possessing terminal alpha-trialkylsilyl groups, are synthesized utilizing concise routes and UV-irradiation to form macrocyclic ring systems. In contrast, the indirect route developed for the synthesis of lariat-type crown ethers employs sequences in which SET-promoted macrocyclization reactions of a-trialkylsilyl-terminated, polyethoxy-tethered phthalimides and naphthalimides are followed by a side chain introduction through substitution reactions at the amidol centers in the macrocyclic ethers. The combined observations made in these investigations demonstrate the unique features of SET-promoted photocyclization reactions that make them well-suited for the use in the synthesis of functionalized crown ethers. In addition, while some limitations exist for the general use of SET-photochemical reactions in large-scale organic synthesis, important characteristics of the photoinduced macrocyclization reactions make them applicable to unique situations in which high temporal and spatial control is required.
URI
http://hdl.handle.net/YU.REPOSITORY/33190http://dx.doi.org/10.3762/bjoc.10.47
ISSN
1860-5397
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이과대학 > 화학생화학부 > Articles
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