Rate Profiling the Impact of Remote Functional Groups on the Redox-Relay Heck Reaction | Zendy

Samantha L. Kraus | Zendy; Sean P. Ross | Zendy; Matthew S. Sigman | Zendy

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Rate Profiling the Impact of Remote Functional Groups on the Redox-Relay Heck Reaction

Author(s) -

Samantha L. Kraus,

Sean P. 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.

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