化学
预酸化
三环己基膦
复分解
硼酸
配体(生物化学)
立体化学
组合化学
有机化学
催化作用
磷化氢
生物化学
受体
酶
聚合
聚合物
作者
George Kwesiga,Julia Greese,Alexandra Kelling,Eric Sperlich,Bernd Schmidt
标识
DOI:10.1021/acs.joc.2c02698
摘要
Isoflavones were synthesized via Suzuki–Miyaura coupling of 3-iodochromones and para-methoxybenzene- and para-phenolboronic acid. In our hands, conditions commonly used for similar cross couplings turned out to be unsuccessful or difficult to reproduce, for example, due to the unplanned partial cleavage of MOM-protecting groups. Using Pd(dba)2 as a precatalyst and tricyclohexylphosphine as an activating ligand, reliable cross-coupling conditions were identified. In all cases, notably higher yields of isoflavones were obtained with para-phenolboronic acid than with para-methoxybenzene boronic acid. This observation and the commercial availability of para-phenolboronic acid suggest that for the synthesis of the important 3′-prenyl- or 3′,5′-diprenylisoflavone substitution pattern a synthetic route that introduces the prenyl substituents after the Pd-catalyzed cross-coupling step, thereby avoiding laborious and protecting-group-intensive multistep syntheses of C-prenylated arene boronic acids, is advantageous.
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