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
Recommended Citation
Nnamdi, Fred U.; Diner, Colin; Champagne, Pier Alexandre; and Organ, Michael G., "Experimental and Computational Study on the Anti-Markovnikov Hydrofunctionalization of Olefins Using Glycine-Extended AQ-Auxiliaries" (2021). Faculty Publications. 4316.
https://digitalcommons.njit.edu/fac_pubs/4316