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

ABSTRACT: 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.

SUBMITTER: Kraus SL

PROVIDER: S-EPMC8026703 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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

Kraus Samantha L SL Ross Sean P SP Sigman Matthew S MS

Organic letters 20210312 7

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 functionaliza ...[more]

PMID: 33710906

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