通过酚类与色胺在水中的交叉环化构建螺环四氢-β-咔啉。
Construction of Spirocyclic Tetrahydro-β-carbolines via Cross-Annulation of Phenols with Tryptamines in Water.
机构信息
The State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 0B8, Canada.
出版信息
Org Lett. 2019 Sep 6;21(17):7033-7037. doi: 10.1021/acs.orglett.9b02613. Epub 2019 Aug 22.
Phenols are readily available by degradation of lignin resource. Palladium-catalyzed conversion of phenols to tetrahydro-β-carboline skeletons bearing a spirocycle at the C-1 position in water is reported. Various substituted phenols are successfully cross-annulated with different tryptamines via sequential C(Ar)-O bond cleavage of phenols, C-H bond activation of tryptamines, and C-N/C-C bond formations. This method provides a new protocol of converting lignin phenols into high-value-added compounds, such as natural product Komavine.
酚类可通过木质素资源的降解而大量获得。本文报道了钯催化的酚转化为在 C-1 位带有螺环的四氢-β-咔啉骨架的反应，该反应在水中进行。通过酚的 C(Ar)-O 键断裂、色胺的 C-H 键活化以及 C-N/C-C 键形成的顺序反应，各种取代的酚类与不同的色胺类化合物成功地进行了交叉环化。该方法提供了一种将木质素酚转化为高附加值化合物（如天然产物 Komavine）的新方法。
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