Tandem arylation and regioselective allylic etherification of 2,3-allenol via Pd/B cooperative catalysis.

Tandem arylation and regioselective allylic etherification of 2,3-allenol via Pd/B cooperative catalysis.

Li, Hongfang;Li, Tao;Hsueh, Yu Jen;Wu, Xue;Xu, Feng;Zhang, Yong Jian;
Organic & biomolecular chemistry 2019
343
li2019tandemorganic

Abstract

An efficient method for the construction of arylated allylic ethers was developed via three-component tandem arylation and allylic etherification of 2,3-allenol with aryl iodides and alcohols. In the cooperative catalytic system of a palladium complex and triethylborane, the process allows rapid access to functionalized 1-arylvinylated 1,2-diol derivatives in good to high yields with complete branch-selectivities. The synthetic utility of the present process was demonstrated by the late-stage functionalization of a drug molecule, the gram-scale synthesis and the elaboration of the products.

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ID: 34811
Ref Key: li2019tandemorganic
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34811
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10.1039/c9ob01792e
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