7363-85-1Relevant academic research and scientific papers
Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates
Huffman, Tucker R.,Wu, Yebin,Emmerich, Alexis,Shenvi, Ryan A.
, p. 2371 - 2376 (2019)
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.
