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Tandem arylation and regioselective allylic etherification of 2,3-allenol via Pd/B cooperative catalysis†
Tao Li,Yu Jen Hsueh,Xue Wu,Feng Xu,Yong Jian Zhang
Organic & Biomolecular Chemistry Pub Date : 08/21/2019 00:00:00 , DOI:10.1039/C9OB01792E
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.

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