4.7 Article

Palladium Nanoparticle-Catalyzed Direct Ethynylation of Aliphatic Carboxylic Acid Derivatives via C(sp3)-H Bond Functionalization

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 7, Pages 1631-1637

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201301180

Keywords

alkynylation; CH bond functionalization; nanoparticles; palladium; recyclable catalysts

Funding

  1. Ministry of Education, Culture, Sports, Science, and Technology, Japan (MEXT)
  2. Grants-in-Aid for Scientific Research [26288051, 25670049, 25105702, 23246013] Funding Source: KAKEN

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We have developed a sulfur-modified, gold-supported palladium material (SAuPd) with palladium, Pd, nanoparticles on its surface; it is a recyclable, low-leaching Pd catalyst. Here we report, using SAuPd, the first example of Pd nanoparticle-catalyzed, unactivated C(sp(3))H bond functionalization of amides, using 8-aminoquinoline as a directing group, to yield ethynylated products. The low leaching properties of SAuPd enabled it to be recycled and reused 10 times for C(sp(3))H bond functionalization.

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