A Lewis‐Acid‐Catalyzed Phenolic Ether ‘O to C’ Rearrangement: Synthesis of 4‐Aryldihydrocoumarins

An efficient O to C rearrangement of phenolic ethers is developed. The Lewis acid BF3⋅OEt2 (0.5 equiv) could catalyze the O to C migration of β‐aryloxy‐β‐arylesters to β,β‐bis‐arylesters, thereby the free phenolic OH cyclizes with the ester group, resulting in the formation of 4‐aryldihydrocoumarins...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2019-07, Vol.8 (7), p.1001-1009
Main Authors: Kumar, Praveen, Kunkalkar, Rupesh A., Fernandes, Rodney A.
Format: Article
Language:English
Subjects:
bioactivity
dihydrocoumarins
Ethers
Lewis acid
Lewis acids
Migration
natural products
Organic chemistry
rearrangement
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Summary:An efficient O to C rearrangement of phenolic ethers is developed. The Lewis acid BF3⋅OEt2 (0.5 equiv) could catalyze the O to C migration of β‐aryloxy‐β‐arylesters to β,β‐bis‐arylesters, thereby the free phenolic OH cyclizes with the ester group, resulting in the formation of 4‐aryldihydrocoumarins. On Call: An efficient O to C rearrangement of β‐aryloxy‐β‐arylesters to β,β‐bis‐arylesters is described. The free phenolic OH group cyclizes with the ester, resulting in the formation of 4‐aryldihydrocoumarins.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900213