92776-51-7Relevant academic research and scientific papers
On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides
Denmark, Scott E.,Werner, Nathan S.
supporting information; experimental part, p. 3612 - 3620 (2010/05/01)
The stereochemical course of palladium-catalyzed cross-coupling reactions of an enantioenriched, a-substituted, allylic silanolate salt with aromatic bromides has been investigated. The allylic silanolate salt was prepared in high geometrical (Z/E, 94:6) and high enantiomeric (94:6 er) purity by a coppercatalyzed SN2′ reaction of a resolved allylic carbamate. Eight different aromatic bromides underwent crosscoupling with excellent constitutional site-selectivity and excellent stereospecificity. Stereochemical correlation established that the transmetalation event proceeds through a syn SE′ mechanism which is interpreted in terms of an intramolecular delivery of the arylpalladium electrophile through a key intermediate that contains a discrete Si-O-Pd linkage.
Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of π-Allyl palladium intermediates under oxidative conditions
Liao, Longyan,Sigman, Matthew S.
supporting information; experimental part, p. 10209 - 10211 (2010/09/05)
A palladium-catalyzed reductive cross-coupling of 1,3-dienes with boronic esters in which a π-allyl Pd species is generated directly from a 1,3-diene via a Pd-catalyzed aerobic alcohol oxidation is reported. Both the scope of the process and the origin of a highly selective 1,2-addition are discussed.
