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Pd‐Senphos Catalyzed trans ‐Selective Cyanoboration of 1,3‐Enynes
Author(s) -
Zhang Yuanzhe,
Li Bo,
Liu ShihYuan
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202005882
Subject(s) - enyne , alkyne , catalysis , chemistry , palladium , combinatorial chemistry , ligand (biochemistry) , tetra , boron , stereochemistry , medicinal chemistry , organic chemistry , receptor , biochemistry
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.