Carboxylate‐Assisted Oxidative Addition to Aminoalkyl Pd II Complexes: C(sp 3 )−H Arylation of Alkylamines by Distinct Pd II /Pd IV Pathway

Autor:	J Henry Blackwell, William G. Whitehurst, Matthew J. Gaunt, Gary N. Hermann
Rok vydání:	2019
Předmět:	Reaction mechanism 010405 organic chemistry Chemistry Decarboxylation chemistry.chemical_element General Chemistry General Medicine 010402 general chemistry 01 natural sciences Medicinal chemistry Oxidative addition Catalysis Reductive elimination 0104 chemical sciences chemistry.chemical_compound Reagent Amine gas treating Carboxylate Palladium
Zdroj:	Angewandte Chemie. 131:9152-9157
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201902838
Popis:	Reported is the discovery of an approach to functionalize secondary alkylamines using 2-halobenzoic acids as aryl-transfer reagents. These reagents promote an unusually mild carboxylate-assisted oxidative addition to alkylamine-derived palladacycles. In the presence of AgI salts, a decarboxylative C(sp3 )-C(sp2 ) bond reductive elimination leads to γ-aryl secondary alkylamines and renders the carboxylate motif a traceless directing group. Stoichiometric mechanistic studies were effectively translated to a Pd-catalyzed γ-C(sp3 )-H arylation process for secondary alkylamines.
Databáze:	OpenAIRE
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