Gold-Catalyzed Synthesis of Tropone and Its Analogues via Oxidative Ring Expansion of Alkynyl Quinols

A new and convenient strategy for
the synthesis of functionalized
tropone derivatives based on the gold-catalyzed oxidative ring expansion
of alkynyl quinols has been developed. The reaction proceeds via gold-catalyzed
highly regioselective oxidation followed by 1,2-migration of a vinyl
or phenyl group. Extension of this chemistry allows ready access to
various seven- or six-membered ring systems such as benzotropones,
benzooxepines, phenanthrenes, and quinolin-2­(1H)-ones.

本研究开发了一种基于炔基奎诺醇（alkynyl quinols）金催化氧化扩环反应，合成官能化卓酮（tropone）衍生物的新颖便捷合成策略。该反应经由金催化的高区域选择性氧化过程，随后发生乙烯基或苯基的1,2-迁移步骤。对该合成方法学的进一步拓展，可便捷获取多种七元或六元环体系化合物，包括苯并卓酮、苯并氧杂卓、菲以及喹啉-2(1H)-酮等。