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

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.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC7491284 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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

Zhang Yuanzhe Y Li Bo B Liu Shih-Yuan SY

Angewandte Chemie (International ed. in English) 20200716 37

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, a ...[more]

PMID: 32511855

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