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1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp(2))-to-N Silyl Migration

Title
1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp(2))-to-N Silyl Migration
Authors
Jeon, Young-KyoKim, Won-Suk
Ewha Authors
김원석
SCOPUS Author ID
김원석scopus
Issue Date
2021
Journal Title
ORGANIC LETTERS
ISSN
1523-7060JCR Link

1523-7052JCR Link
Citation
ORGANIC LETTERS vol. 23, no. 19, pp. 7545 - 7549
Publisher
AMER CHEMICAL SOC
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp(2))-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%.
DOI
10.1021/acs.orglett.1c02751
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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