Poly(dimethylsiloxane)-Based Recyclable Tablet Catalysts Bearing Gold N-Heterocyclic Carbene Complexes for Alkyne Hydration Reactions

Tunali Z., Dagistanli S., Kubalas S., ÖZTÜRK B. Ö.

Organic Process Research and Development, cilt.27, sa.7, ss.1300-1307, 2023 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 27 Sayı: 7
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1021/acs.oprd.3c00064
  • Dergi Adı: Organic Process Research and Development
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Compendex
  • Sayfa Sayıları: ss.1300-1307
  • Anahtar Kelimeler: alkyne hydration, gold, N-heterocyclic carbene, poly(dimethylsiloxane), tablet catalyst
  • Hacettepe Üniversitesi Adresli: Evet

Özet

The tablet-based catalytic systems offer various advantages such as improved stability, ease of handling, and dosage delivery of transition metal catalysts for organic transformation reactions. The traditional paraffin wax-based tablet catalysts are useful in storing and dosage delivery of organometallic catalysts; however, the recycling of the catalyst is not possible due to the solubility of wax in common organic solvents. In this study, we have developed poly(dimethylsiloxane) (PDMS)-based recyclable tablet catalyst systems bearing gold(I) N-heterocyclic carbene complexes for alkyne hydration reactions in the aqueous medium. Commercial PDMS rods, room-temperature vulcanizable universal silicones, and Pattex were used as tablet materials. The tablet catalysts showed high performance in the hydration of both alkyl and aryl acetylene derivatives and can easily be isolated from the reaction media in the solid phase. The tablet catalyst can be reused up to the 13th turn in the hydration of phenylacetylene in a methanol/water medium.