Ruthenium-catalyzed 1,3-indolyl migration within α,α-disubstituted allylic alcohols

The functional group migration strategy could facilitate the construction of complex structures from relatively simple starting materials. In contrast to the well-developed transition-metal catalyzed intramolecular 1,3-hydride migration, 1,3-carbon migration in allylic alcohols is marginally less re...

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Veröffentlicht in:Organic Chemistry Frontiers 2023-03, Vol.10 (7), p.1705-1709
Hauptverfasser: Zhang, Xue, Luo, Zhen, Liu, Tang-Lin, Li, Qing-Hua
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Sprache:eng
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Zusammenfassung:The functional group migration strategy could facilitate the construction of complex structures from relatively simple starting materials. In contrast to the well-developed transition-metal catalyzed intramolecular 1,3-hydride migration, 1,3-carbon migration in allylic alcohols is marginally less reported. Herein, we report a protocol for Ru-catalyzed 1,3-indolyl migration under mild conditions. In this study, we disclosed that indoles have better migration ability than phenyl groups. Overall, this catalytic system enabled the simultaneous selective C(sp 3 )–C(sp 2 ) bond cleavage and reconstruction, which allow for an immediate synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields.
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/D3QO00049D