钌催化的1,3-吲哚基在α,α-二取代烯丙醇中的迁移

Xue Zhang , Zhen Luo , Tang-Lin Liu , Qing-Hua Li
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摘要

官能团迁移策略可以促进从相对简单的起始材料构建复杂的结构。与发展良好的过渡金属催化的分子内1,3-氢化物迁移相比,烯丙醇中的1,3-碳迁移的报道略少。在此,我们报道了在温和条件下Ru催化的1,3-吲哚基迁移的方案。在这项研究中,我们发现吲哚比苯基具有更好的迁移能力。总的来说,该催化体系能够同时选择性地切割和重建C(sp3)-C(sp2)键,从而能够以广泛的底物范围和合理的产率立即合成β-吲哚酮。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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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 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(sp3)–C(sp2) bond cleavage and reconstruction, which allow for an immediate synthesis of β-indolyl ketones with a broad substrate scope and reasonable yields.

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Synthesis of biologically active [1,5]diazocino[2,1-b]quinazolinones through [4 + 4] cycloaddition of 2-alkynyl quinazolinones with aza-ortho-quinone methides† Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols† Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes† Playing with the cavity size of exTTF-based self-assembled cages† An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex†
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