Journal
ORGANOMETALLICS
Volume 40, Issue 8, Pages 1032-1041Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.1c00024
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Funding
- National Natural Science Foundation of China [21972045, 21673077]
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The study investigates the mechanism of Pd-catalyzed amino dicarbonylation of aryl halides using different ligands, with the ionic diphosphine ligand L4 showing superior catalytic performance for achieving high conversion rates and selectivity.
The amino dicarbonylation of aryl halides affording a-ketoamides with Pd catalysts is highly dependent on the stereoelectronic properties of the involved ligands. Ionic diphosphine ligand L4 can serve as precursor of a hemilabile P,C (phosphine, carbene)-hybrid ligand to form a stable Pd(II)-complex, Pd-L4. In contrast, analogues L1-L3 with a similar 1-(thiophen-3-yl)-benzimidazolyl skeleton behave as typical (mono/di)phosphines. The catalytic system resulting from the complexation of PdCl2 (MeCN)(2) and L4 exhibits good catalytic performance in terms of aryl iodides conversion (81-95%) and alpha-ketoamide selectivity (80-91%), as well as the available recyclability in the RTIL of [Bpy]BF4. The in situ FT-IR analysis reveals that the PdCl2 (MeCN)(2)-L4 catalytic system favors the amino dicarbonylation toward alpha-ketoamides according to the proposed mechanism of cycle I, which involves two independent CO-insertion steps.
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