4.8 Article

Strain-Induced Double Carbon-Carbon Bond Activations of Cycloparaphenylenes by a Platinum Complex: Application to the Synthesis of Cyclic Diketones

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 35, Pages 11418-11421

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806591

Keywords

carbonylation; C-C activation; cycloparaphenylenes; platinum; strained molecules

Funding

  1. Japan Society for the Promotion of Science (JSPS) KAKENHI Grant [18H01962, 16H06352]
  2. Collaborative Research Program of Institute for Chemical Research (ICR), Kyoto University (KU) [2018-36]
  3. Super Computer Laboratory, ICR, KU

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The carbon-carbon (C-C) bond activation of [n]cycloparaphenylenes ([n]CPPs) by a transition-metal complex is herein reported. The Pt-0 complex Pt(PPh3)(4) regioselectively cleaves two C-C sigma bonds of [5] CPP and [6]CPP to give cyclic dinuclear platinum complexes in high yields. Theoretical calculations reveal that the relief of ring strain drives the reaction. The cyclic complex was further transformed into a cyclic diketone by using a CO insertion reaction.

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