Substituent-Determined Intramolecular Hydrogen Transfer for Photopromoted Intermolecular Cycloaddition of
Fanyuanhang Yang1,2, Ping Lin1, Biping Xu1
1State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, China.
Abstract:
The formation of intramolecular hydrogen bonds in anthraquinones makes them inert to photoinduced reactions; therefore, it is a great challenge to phototransform these compounds. Herein, we reported a formal visible-light-induced [4 + 2] cycloaddition of both 1-hydroxyanthraquinones and 1-aminoanthraquinones with olefins under external photocatalyst-free conditions with high regioselectivity. More than 60 substrates are disclosed, demonstrating the reliability of this protocol to construct diverse functionalized anthraquinone derivatives.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.


