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. 2019 Jul 1;58(27):9054-9059.
doi: 10.1002/anie.201902838. Epub 2019 May 24.

Carboxylate-Assisted Oxidative Addition to Aminoalkyl PdII Complexes: C(sp3 )-H Arylation of Alkylamines by Distinct PdII /PdIV Pathway

William G Whitehurst  1 , J Henry Blackwell  1 , Gary N Hermann  1 , Matthew J Gaunt  1
Affiliations

Carboxylate-Assisted Oxidative Addition to Aminoalkyl PdII Complexes: C(sp3 )-H Arylation of Alkylamines by Distinct PdII /PdIV Pathway

William G Whitehurst et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: C−H activation; amines; decarboxylation; palladium; reaction mechanisms.

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