Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis.,Organic Letters

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Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis.
Organic Letters ( IF 4.9 ) Pub Date : 2020-06-18 , DOI: 10.1021/acs.orglett.0c01329
Nicholas R Lee ₁ , Farbod A Moghadam ₁ , Felipe C Braga ₁ , Daniel J Lippincott ₁ , Bingchun Zhu ₁ , Fabrice Gallou ₂ , Bruce H Lipshutz ₁

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Palladium-catalyzed allylic substitution, or “Tsuji–Trost” reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N–H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.

中文翻译：

水胶束催化实现的可持续钯催化的Tsuji-Trost反应。

钯催化的烯丙基取代或“ Tsuji–Trost”反应可在胶束催化条件下进行，该条件不仅具有水中的化学性质，而且具有需要低钯含量（通常约为1000 ppm（0.1）的反应伙伴的众多组合）摩尔％）。这些偶联的特征还在于特别温和的条件，导致许多以前在胶束水性介质中没有报道的病例。描述了包含各种亲核试剂，例如NH杂环，醇，二羰基化合物和磺酰胺。分子内环化进一步说明了该方法的广泛用途。除了回收研究之外，还报告了一个多克规模的示例，该示例表明了扩大规模的前景。

更新日期：2020-07-02

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