The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Methoxypiperidine( cas:4045-24-3 ) is researched.Name: 4-Methoxypiperidine.An, Yang; Li, Yuke; Zhang, Xiao-Yan; Zhang, Zhe; Gou, Xue-Ya; Ding, Ya-Nan; Li, Qiao; Liang, Yong-Min published the article 《Palladium-Catalyzed C-H Amination/[2+3] or [2+4] Cyclization via C(sp3 or sp2)-H Activation》 about this compound( cas:4045-24-3 ) in Organic Letters. Keywords: amino fused bicyclic compound preparation regioselective; iodoarene benzoyloxyamine norbornadiene Catellani reaction amination cyclization palladium catalyst. Let’s learn more about this compound (cas:4045-24-3).
This report describes a palladium-catalyzed Catellani reaction consisting of amination/[2+3] or [2+4] cyclization via a carboxylate ligand-exchange strategy. This method effectively activates ortho-substituents that avoid a second C-H palladation. The scope of substrates was broad, o-methyl-substituted iodoarenes R-2-CH3-C6H3I (R = H, 4-F, 3-Me, 4-Cl, etc.), 3-iodo-4-methyl-pyridine were applied to the reaction smoothly, and o-phenyl-substituted iodoarenes 2-I-C6H4-(4-R1C6H4-) (R1 = H, Me, Ph, F, etc.), 1-(2-iodo-phenyl)-naphthalene can also be obtained by this method. In terms of mechanism, d. functional theory calculations proved the sequence of the key five-membered aryl-norbornene-palladacycle intermediate formation and C(sp3 or sp2)-H activation.
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Reference:
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