"Experimental and Computational Study on the Anti-Markovnikov Hydrofunc" by Fred U. Nnamdi, Colin Diner et al.
 

Experimental and Computational Study on the Anti-Markovnikov Hydrofunctionalization of Olefins Using Glycine-Extended AQ-Auxiliaries

Document Type

Article

Publication Date

2-19-2021

Abstract

Two similar tridentate directing groups derived from glycine and 8-aminoquinoline were shown to enable the palladium-catalyzed anti-Markovnikov hydrofunctionalization of 4-pentenylamine with drastically different efficiencies. A computational investigation into the origin of the reactivity difference between these isomeric, carbonyl-transposed auxiliaries suggests that protonation state, thus charge of the substrate-metal complex prior to nucleopalladation is key. These investigations have culminated in a directing group design that can undergo Pd-catalyzed hydrofunctionalization under relatively mild conditions, as low as room temperature.

Identifier

85099956790 (Scopus)

Publication Title

Chemistry A European Journal

External Full Text Location

https://doi.org/10.1002/chem.202004881

e-ISSN

15213765

ISSN

09476539

PubMed ID

33617055

First Page

3855

Last Page

3860

Issue

11

Volume

27

Grant

05584

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