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  • Visible Light-Assisted Ring-Opening of Cyclic Ethers with Carboxylic Acids Mediated by Triphenylphosphine and N-Halosuccinimides
Title: Visible Light-Assisted Ring-Opening of Cyclic Ethers with Carboxylic Acids Mediated by Triphenylphosphine and N-Halosuccinimides
The ring-opening of cyclic ethers (epoxide, oxetane, THF, and THP) by carboxylic acids was achieved by using N-iodosuccinimide (NIS) or N-bromosuccinimide (NBS) and triphenylphosphine under the irradiation of blue light. The corresponding omega-haloalkyl carboxylates were obtained under mild reaction conditions. The reaction is believed to work through a halogen bond complex between NIS (or NBS) and triphenylphosphine, which, upon irradiation with blue light, produces the key phosphine radical cation intermediate that initiates the ring-opening reactions.  more » « less
Award ID(s):
1664278
PAR ID:
10483869
Author(s) / Creator(s):
; ; ; ; ;
Publisher / Repository:
American Chemical Society
Date Published:
Journal Name:
Organic Letters
ISSN:
1523-7060
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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