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1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration

Title
1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration
Authors
Jeon Y.-K.Kim W.-S.
Ewha Authors
김원석
SCOPUS Author ID
김원석scopusscopus
Issue Date
2021
Journal Title
Organic Letters
ISSN
1523-7060JCR Link
Citation
Organic Letters vol. 23, no. 19, pp. 7545 - 7549
Publisher
American Chemical Society
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp2)-to-N 1,3-aza-Brook rearrangement have been achieved, allowing access to diverse aniline derivatives. Through crossover experiments, we demonstrated the intramolecular mechanism of 1,3-C-to-N silyl transfer. To gain insight into the regioselectivity observed in the reactions, we performed density functional theory calculations. Finally, the method was applied to the synthesis of xylanigripones A in five linear steps in an overall yield of 30%. © 2021 American Chemical Society.
DOI
10.1021/acs.orglett.1c02751
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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