Mechanistic Studies of Pd(II)-Catalyzed E/Z Isomerization of Unactivated Alkenes: Evidence for a Monometallic Nucleopalladation Pathway

09 November 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Pd(II)-catalyzed E/Z isomerization of alkenes is a common process—yet is largely uncharacterized, particularly with non-conjugated alkenes. In this work, the mechanism of Pd(II)-catalyzed E/Z isomerization of unactivated olefins containing an aminoquinoline-based amide directing group is probed using in situ kinetic analysis, spectroscopic studies, kinetic modeling, and DFT calculations. The directing group allows for stabilization and monitoring of previously undetectable intermediates. Collectively, the data are consistent with isomerization occurring through a monometallic nucleopalladation mechanism.


Alkene Isomerization
Mechanistic Elucidation
Directing Group

Supplementary materials

Supporting Info


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