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Synlett 2022; 33(13): 1266-1272
DOI: 10.1055/a-1827-6915
DOI: 10.1055/a-1827-6915
letter
Divergent Thio/Selenolactonization of Styrene-Type Carboxylic Acids and Amides: Synthesis of Chalcogenated Isobenzofuran-1 (3H)-ones and Isochroman-1-ones
K.Z. acknowledges the National Key Research and Development Program of China (2019YFA0905104), and Y.D. acknowledges the National Natural Science Foundation of China (#22071175) for financial support.
Abstract
A divergent synthesis of isobenzofuran-1(3H)-one and 3,4-dihydroisochroman-1-one derivatives has been realized through the reaction of o-alkenyl benzoic acids/amides with PhICl2 and diphenyl disulfides/diselenides. Depending on the substitution type of the o-alkenyl benzoic acid or amide, this metal-free intramolecular oxychalcogenation approach regioselectively affords isobenzofuran-1(3H)-ones or 3,4-dihydroisochroman-1-ones through 5-exo-trig or 6-endo-trig cyclization processes, respectively.
Key words
isobenzofuranones - isochromanones - thiolactonization - selenolactonization - chalcogenationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1827-6915.
- Supporting Information
Publication History
Received: 12 January 2022
Accepted after revision: 18 April 2022
Accepted Manuscript online:
18 April 2022
Article published online:
20 May 2022
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