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Issue 11, 2013
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Pd(II)-catalyzed alkoxylation of unactivated C(sp3)–H and C(sp2)–H bonds using a removable directing group: efficient synthesis of alkyl ethers

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Abstract

The Pd(II)-catalyzed alkoxylation of unactivated C(sp3)–H and C(sp2)–H bonds using a new bidentate directing group has been developed. Alkoxylation occurs selectively at the β position with broad substrate scope and high tolerance of functional groups (chloro, cyano, ether, ester, olefin, amino, etc.). Besides alkoxylation of the β-C–H bonds, γ-alkoxylation of C(sp2)–H bonds could also be achieved, provided that no reactive β-C–H bonds were present. In addition, this DG is readily available and removable.

Graphical abstract: Pd(ii)-catalyzed alkoxylation of unactivated C(sp3)–H and C(sp2)–H bonds using a removable directing group: efficient synthesis of alkyl ethers

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Publication details

The article was received on 16 Jul 2013, accepted on 09 Aug 2013 and first published on 09 Aug 2013


Article type: Edge Article
DOI: 10.1039/C3SC51993G
Citation: Chem. Sci., 2013,4, 4187-4192
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    Pd(II)-catalyzed alkoxylation of unactivated C(sp3)–H and C(sp2)–H bonds using a removable directing group: efficient synthesis of alkyl ethers

    F. Chen, S. Zhao, F. Hu, K. Chen, Q. Zhang, S. Zhang and B. Shi, Chem. Sci., 2013, 4, 4187
    DOI: 10.1039/C3SC51993G

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