One-Pot Construction of Heteroarylation/Esterification Products of Acrylic Acids via Iridium(III)-Catalyzed C–H Activation

A carboxylate-assisted iridium­(III)-catalyzed regioselective C­(sp2)–H heteroarylation/esterification reaction of acrylic acid is disclosed herein for the first time. This catalytic protocol tolerates various α-substituted, β-substituted, and α, β-disubstituted acrylic acids as well as heteroaromat...

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Veröffentlicht in:Organic letters 2022-12, Vol.24 (48), p.8747-8752
Hauptverfasser: Wu, Jia-Xue, Wang, Huai-Wei, Duan, Wen-Zeng, Ji, Hong-Han, Dou, Jian-Min, Huang, Xian-Qiang, Lu, Yi, Li, Da-Cheng
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Sprache:eng
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Zusammenfassung:A carboxylate-assisted iridium­(III)-catalyzed regioselective C­(sp2)–H heteroarylation/esterification reaction of acrylic acid is disclosed herein for the first time. This catalytic protocol tolerates various α-substituted, β-substituted, and α, β-disubstituted acrylic acids as well as heteroaromatic boronates well. The resulting 3,4-dihydro-2H-pyran-6-carboxylic acid derivative 3r highlighted the AIE-active luminophore with multiple emission signal properties and a high quantum yield of 28%, exhibiting the potential application of this methodology for the synthesis of nitrogen-containing organic functional materials.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03245