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Updated: Jun 13, 2025

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Bis(imidazolidine)-Derived NCN Nickel-Pincer-Catalyzed Asymmetric Reactions
Tomoya Yokota1, Yan Yu1, Kensuke Araseki1
1Soft Molecular Activation Research Center (SMARC), Chiba Iodine Resource Innovation Center (CIRIC), Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Abstract:
A bis(imidazolidine)-derived NCN nickel-pincer complex (tBu-PhBidine-Ni-OTf: NCN-Ni-OTf) was synthesized by the oxidative addition of imidazolidine-containing aryl triflate to Ni(cod)2 in MeCN. NCN-Ni-OTf exhibited asymmetric induction in three reactions. In the Friedel-Crafts reaction of indoles with N-Boc imines, 3-indolylmethanamine products were obtained in 79% yield with 99% ee. In a conjugate addition reaction of malononitrile to nitroalkenes, products were obtained in 95% yield with 75% ee. In iodolactonization, the pincer-Ni complex showed catalytic activity superior to that of tBu-PhBidine-Pd-OTf.
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