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

Autor:	Pier Alexandre Champagne, Colin Diner, Michael G. Organ, Fred U. Nnamdi
Rok vydání:	2021
Předmět:	010405 organic chemistry Chemistry Organic Chemistry Markovnikov's rule chemistry.chemical_element Protonation General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Glycine Reactivity (chemistry) Palladium
Zdroj:	Chemistry – A European Journal. 27:3855-3860
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.202004881
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3be44822b32b9b271a4028cec65b591c https://doi.org/10.1002/chem.202004881 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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