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. 2023 Jul;88(7):e202300231.
doi: 10.1002/cplu.202300231.

Shape Selectivity in the Gold-Catalyzed Hydration of Alkynes Using a Cavity-Shaped Phosphine

Miquel Navarro  1 , Markus Holzapfel  1   2 , Jesús Campos  1
Affiliations

Shape Selectivity in the Gold-Catalyzed Hydration of Alkynes Using a Cavity-Shaped Phosphine

Miquel Navarro et al. Chempluschem. 2023 Jul.

Abstract

A cavity-shaped gold(I) complex derived from a bulky tri-(ortho-biaryl)-phosphine ligand shows preferred selectivity towards terminal functionalities in the gold(I)-catalysed hydration of alkynes under mild heating due to a well-defined pocket as catalytic active site. The confinement-induced size-exclusion selectivity investigated for eight alkynes contrasts with other gold(I) complexes bearing bulky phosphine ligands that show reduced selectivity or even similar behaviour towards both internal and terminal alkynes. We also interrogate the potential of gold(III) derivatives for the same catalytic process.

Keywords: Alkynes; gold; homogeneous catalysis; hydration; phosphines.

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