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Defective NiO Nanoparticles Supported on Nb 2 O 5 for Solid‐Catalyzed Markovnikov‐Selective Hydroboration of Styrenes

Ayako Taketoshi,Yusei Kimura,Eiji Hirano,Norihito Sakaguchi,Tamao Ishida,Toru Murayama,Y. Yamaguchi

Published 2025 in Annalen der Pharmacie

ABSTRACT

Markovnikov selective hydroboration of alkenes with an air‐ and moisture‐stable diboron reagent is a more challenging reaction than the anti ‐Markovnikov‐selective one. We report that nickel oxide (NiO) supported on niobium pentoxide (Nb 2 O 5 ) efficiently catalyzed the hydroboration of 4‐ tert ‐butylstyrene, affording a Markovnikov (branched) adduct with excellent selectivity. To the best of our knowledge, this is the first report of the Markovnikov‐selective hydroboration of styrenes with a diboron reagent, bis(pinacolato)diboron, using a solid catalyst. NiO on Nb 2 O 5 contains Ni 3+ , which is more catalytically active than Ni 2+ , as a major species in contrast to bulk NiO. However, the catalytic activity decreased upon recycling tests because the Ni species leached from NiO/Nb 2 O 5 . The catalytically active species were NiO on Nb 2 O 5 and leached Ni species. To improve the reusability of the catalyst system, NiO/Nb 2 O 5 , ZnO was introduced as a redeposition site for the leached Ni species. Ultimately, the desired Markovnikov adduct was obtained in high yield and selectivity using NiO/Nb 2 O 5 in the presence of ZnO (92% yield and 92% selectivity), and catalyst reusability was also improved.

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