RP(O)H 与三芳基甲醇之间的高效亲核取代反应合成磷取代的三芳基甲烷。

A highly efficient nucleophilic substitution reaction between RP(O)H and triarylmethanols to synthesize phosphorus-substituted triarylmethanes.

机构信息

Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics Chengdu University, 168 Hua Guan Road, Chengdu 610052, P. R. China.

出版信息

Org Biomol Chem. 2018 Feb 7;16(6):951-956. doi: 10.1039/c7ob02970e.

DOI:10.1039/c7ob02970e

PMID:29340404

Abstract

A highly efficient and general nucleophilic substitution reaction between dialkyl H-phosphonates or diarylphosphine oxides and triarylmethanols catalyzed by HOTf (trifluoromethanesulfonic acid) has been developed. It provides an atom-economical protocol for the synthesis of various symmetrical and unsymmetrical phosphorus-substituted triarylmethanes that constitute an emerging family of potent anticancer agents in rich diversity with 40 to 96% yields. The synthetic applicability of this protocol is demonstrated by gram-scale preparations.

摘要

一种高效且通用的亲核取代反应，在 HOTf（三氟甲磺酸）的催化下，二烷基 H-膦酸酯或二芳基氧化膦与三芳基甲醇之间发生反应。该反应为合成各种对称和不对称的磷取代三芳基甲烷提供了一种原子经济性的方法，这些三芳基甲烷是一类新兴的具有丰富多样性的有效抗癌药物，产率为 40%至 96%。该方法的合成适用性通过克级制备得到了证明。