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Arylative Allenol Cyclization via Sequential One‐pot Enzyme & Palladium Catalysis
Author(s) -
Naapuri Janne M.,
Åberg Gustav A.,
Palomo Jose M.,
Deska Jan
Publication year - 2021
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202001619
Subject(s) - palladium , chemistry , catalysis , biocatalysis , combinatorial chemistry , halogenation , aqueous solution , halide , organic chemistry , ionic liquid
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.