Arylative Allenol Cyclization via Sequential One-pot Enzyme & Palladium Catalysis

Janne M. Naapuri, Gustav A. Åberg, Jose M. Palomo, Jan Deska*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)

Abstract

The one-pot combination of halogenation biocatalysis and Suzuki-type cross coupling enables the direct arylative cyclization of allenic alcohols with boronic acids. This modular approach to unsaturated five-membered O-heterocycles proceeds in an aqueous emulsion with air as terminal oxidant. Here, the enzymatic oxidative activation of simple halide salts acts as traceless ring-closure-inducing event to trigger the subsequent C−C coupling. With the original protocol merging soluble proteins and a homogeneous SPhos-based palladium catalyst as a template, a novel heterogeneous nanobiohybrid was developed. Consisting of an oxidase matrix hosting small spherical palladium nanoparticles, this enzyme-metal hybrid exhibits catalytic competence for both the biocyclization as well as the C−C bond-forming cross coupling, underlining the potential of this new techniques for streamlining chemoenzymatic approaches.

Original languageEnglish
Pages (from-to)763-769
Number of pages7
JournalChemCatChem
Volume13
Issue number2
Early online date4 Nov 2020
DOIs
Publication statusPublished - 20 Jan 2021
MoE publication typeA1 Journal article-refereed

Keywords

  • cascades
  • chemoenzymatic
  • cross coupling
  • heterocycles
  • nanoparticles

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