Biomaterial Database

Stereocontrolled synthesis of (E)-stilbene derivatives by palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. 2018

Hailee H Rau, and Nathan S Werner

Department of Physical Science, Southern Utah University, 351 W University Blvd, Cedar City, UT 84720, USA.

A general procedure for the stereocontrolled synthesis of (E)-stilbene derivatives by palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (E)-2-phenylethenylboronic acid pinacol ester with aryl bromides was investigated. (E)-2-Phenylethenylboronic acid pinacol ester was prepared by 9-BBN-catalyzed hydroboration of phenylacetylene with pinacolborane. This reagent undergoes facile palladium-catalyzed cross-coupling with a diverse set of aryl bromides to provide the corresponding (E)-stilbene derivatives in moderate to good yield. The use of the sterically bulky t-Bu3PHBF4 ligand was crucial to the successful coupling of electron-rich and electron-poor aryl bromides. Complete stereochemical retention of the (E)-2-phenylethenylboronic acid pinacol ester alkene geometry was observed in all of the (E)-stilbene derivatives synthesized.

UI	MeSH Term	Description	Entries
D010165	Palladium	A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D001897	Boronic Acids	Inorganic or organic compounds that contain the basic structure RB(OH)2.	Boronic Acid,Acid, Boronic,Acids, Boronic
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013267	Stilbenes	Organic compounds that contain 1,2-diphenylethylene as a functional group.	Stilbene,Stilbene Derivative,Stilbene Derivatives,Stilbenoid,Stilbenoids,Derivative, Stilbene,Derivatives, Stilbene