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Gold-catalysed oxyarylation of styrenes and mono- and gem-disubstituted olefins facilitated by an iodine(III) oxidant

机译:碘(III)氧化剂促进金在苯乙烯,单-和双-和双-取代的烯烃上的催化氧化

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摘要

1-Hydroxy-1,2-benziodoxol-3(1H)-one (IBA) is an efficient terminal oxidant for gold-catalysed, three-component oxyarylation reactions. The use of this iodine(III) reagent expands the scope of oxyarylation to include styrenes and gem-disubstituted olefins, substrates that are incompatible with the previously reported Selectfluor-based methodology. Diverse arylsilane coupling partners can be employed, and in benzotrifluoride, homocoupling is substantially reduced. In addition, the IBA-derived co-products can be recovered and recycled. The I's have it: The unprecedented use of an iodine(III) reagent as the terminal oxidant for gold-catalysed oxyarylation allows the substrate scope to be significantly expanded; in addition to monosubstituted olefins, styrenes and gem-disubstituted olefins are well tolerated (see scheme). With benzotrifluoride as solvent, unproductive homodimerisation of the arylsilane coupling partner is effectively suppressed.
机译:1-Hydroxy-1,2-benziodoxol-3(1H)-one(IBA)是一种用于金催化的三组分氧化芳基化反应的有效末端氧化剂。这种碘(III)试剂的使用扩展了氧化芳基化的范围,使其包括苯乙烯和双取代的宝石烯烃,这些底物与先前报道的基于Selectfluor的方法不兼容。可以使用不同的芳基硅烷偶联剂,并且在苯并三氟化物中,均偶联显着减少。此外,IBA衍生的副产品可以回收和再循环。我拥有它:前所未有地使用碘(III)试剂作为金催化的氧化芳基化反应的终端氧化剂,可以大大扩展底物的范围;除单取代的烯烃外,苯乙烯和吉二取代的烯烃均具有良好的耐受性(参见方案)。使用苯并三氟化物作为溶剂,可以有效地抑制芳基硅烷偶联剂的非生产性均二聚。

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