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Issue 7, 2019
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Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes

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Catalysts capable of heterolytic silane activation have been successfully applied to the conversion of alkyl ethers to silyl ethers via C–O bond cleavage. The previously-reported cationic pincer-supported iridium complex for this transformation suffers from poor selectivity with regard to monodealkylation of substrate ethers. We demonstrate that a simple non-pincer iridium complex offers improved selectivity and is capable of benzylic ether cleavage in the presence of reductively-labile alkyl and aryl halide functionality. Preliminary mechanistic experiments suggest a neutral tetrahydridosilyliridium resting state which is consistent with previous mechanistic hypotheses. These experiments suggest that a pincer ligand framework is not required for activity in ether cleavage reactions and that simple cationic bis(phosphine)iridium complexes may offer improved selectivity profiles for applications to more-complex substrate molecules.

Graphical abstract: Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes

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Publication details

The article was received on 17 Sep 2018, accepted on 31 Oct 2018 and first published on 31 Oct 2018

Article type: Communication
DOI: 10.1039/C8OB02298D
Citation: Org. Biomol. Chem., 2019,17, 1744-1748

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    Selective alkyl ether cleavage by cationic bis(phosphine)iridium complexes

    C. A. H. Jones and N. D. Schley, Org. Biomol. Chem., 2019, 17, 1744
    DOI: 10.1039/C8OB02298D

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