Pd-Senphos Catalyzed trans-Selective Cyanoboration of 1,3-Enynes.

Angewandte Chemie
Yuanzhe ZhangShih-Yuan Liu

Abstract

The first trans-selective cyanoboration reaction of an alkyne, specifically a 1,3-enyne, is described. The reported palladium-catalyzed cyanoboration of 1,3-enynes is site-, regio-, and diastereoselective, and is uniquely enabled by the 1,4-azaborine-based Senphos ligand structure. Tetra-substituted alkenyl nitriles are obtained providing useful boron-dienenitrile building blocks that can be further functionalized. The utility of our method has been demonstrated with the synthesis of Satigrel, an anti-platelet aggregating agent.

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Citations

Apr 29, 2021·Chemical Communications : Chem Comm·Floris ButtardPier Alexandre Champagne
Aug 3, 2021·Advanced Synthesis & Catalysis·Ayan BhattacharjeeGary A Molander
Aug 3, 2021·The Journal of Organic Chemistry·Yongkang GuoXuguang Liu
Aug 17, 2021·Organic Letters·Xing ChenWei Zeng
Jul 11, 2021·Angewandte Chemie·Ziyong WangShih-Yuan Liu

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