Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates.

ABSTRACT: Pd⁰ -catalyzed Mizoroki-Heck reactions traditionally exhibit poor reactivity with polysubstituted, unbiased alkenes. Intermolecular reactions with simple, all-carbon tetrasubstituted alkenes are unprecedented. Herein we report that pendant carboxylic acids, combined with bulky monophospine ligands on palladium, can direct the arylation of tri- and tetrasubstituted olefins. Quaternary carbons are established at high Fsp³ attached-ring junctures and the carboxylate directing group can be removed after coupling. Carboxylate directivity prevents over-arylation of the new, less substituted alkene, which can be diversified in subsequent reactions.

SUBMITTER: Huffman TR 

PROVIDER: S-EPMC6370521 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature