1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp(2))-to-N Silyl Migration
- 주제(기타) Chemistry, Organic
- 설명문(일반) [Jeon, Young-Kyo; Kim, Won-Suk] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 03760, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2021
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000183660
- 본문언어 영어
- Published As http://dx.doi.org/10.1021/acs.orglett.1c02751
- PubMed https://pubmed.ncbi.nlm.nih.gov/34553933
초록/요약
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%.
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