Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada.
Angew Chem Int Ed Engl. 2019 Apr 1;58(15):5085-5089. doi: 10.1002/anie.201814660. Epub 2019 Mar 5.
We report a new strategy for the conversion of carboxylic acids into potent acid triflate electrophiles. The reaction involves oxidative carbonylation of carboxylic acids with I in the presence of AgOTf, and is postulated to proceed via acyl hypoiodites that react with CO to form acid triflates. Coupling this chemistry with subsequent trapping with arenes offers a mild, room temperature approach to generate ketones directly from broadly available carboxylic acids without the use of corrosive and reactive Lewis or Bronsted acid additives, and instead from compounds that are readily available, stable, and functional group compatible.
我们报告了一种将羧酸转化为强效酸三氟甲磺酸酯亲电试剂的新策略。该反应涉及在 AgOTf 的存在下用 I 对羧酸进行氧化羰基化，据推测该反应通过酰基次碘酸盐进行，酰基次碘酸盐与 CO 反应形成酸三氟甲磺酸酯。将这种化学与随后与芳烃的捕获相结合，提供了一种温和的、室温下的方法，可直接从广泛可用的羧酸中生成酮，而无需使用腐蚀性和反应性的路易斯或布朗斯台德酸添加剂，而是使用易于获得、稳定且官能团兼容的化合物。
