Open AccessRate Profiling the Impact of Remote Functional Groups on the Redox-Relay Heck Reaction
Author(s) -
Samantha L. Kraus,
Scott R. Ross,
Matthew S. Sigman
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c00450
Subject(s) - stereocenter , chemistry , alkene , heck reaction , relay , combinatorial chemistry , redox , surface modification , functional group , diene , organic chemistry , catalysis , palladium , enantioselective synthesis , polymer , power (physics) , physics , quantum mechanics , natural rubber
The redox-relay Heck reaction is a powerful method for the construction of enantioenriched quaternary stereocenters remote from existing functional groups. However, there has been little success in the design of site-selective alkene functionalization based on these methods. Herein, we show that experimentally determined rates can be used to train a multivariate linear regression model capable of predicting the rate of a specific relay Heck reaction, allowing for the site-selective functionalization of diene substrates.