Organic Letters

, volume 21 , issue 10 , pages 3692-3695

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C–H Methoxylation and Chlorination of Benzaldehydes

Feng Li ¹

Yirong Zhou ²

Heng Yang ¹

Ziqi Wang ¹

Qinqin Yu ¹

Fang Lin Zhang ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, China |

Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China |

Publication type: Journal Article

Publication date: 2019-05-08

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.9b01158

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PubMed ID: 31066562

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.

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G. Petros

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Li F. et al. Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C–H Methoxylation and Chlorination of Benzaldehydes // Organic Letters. 2019. Vol. 21. No. 10. pp. 3692-3695.

GOST all authors (up to 50) Copy

Li F., Zhou Y., Yang H., Wang Z., Yu Q., Zhang F. L. Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C–H Methoxylation and Chlorination of Benzaldehydes // Organic Letters. 2019. Vol. 21. No. 10. pp. 3692-3695.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.9b01158

UR - https://doi.org/10.1021/acs.orglett.9b01158

TI - Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C–H Methoxylation and Chlorination of Benzaldehydes

T2 - Organic Letters

AU - Li, Feng

AU - Zhou, Yirong

AU - Yang, Heng

AU - Wang, Ziqi

AU - Yu, Qinqin

AU - Zhang, Fang Lin

PY - 2019

DA - 2019/05/08

PB - American Chemical Society (ACS)

SP - 3692-3695

IS - 10

VL - 21

PMID - 31066562

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Li,

author = {Feng Li and Yirong Zhou and Heng Yang and Ziqi Wang and Qinqin Yu and Fang Lin Zhang},

title = {Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C–H Methoxylation and Chlorination of Benzaldehydes},

journal = {Organic Letters},

year = {2019},

volume = {21},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/acs.orglett.9b01158},

number = {10},

pages = {3692--3695},

doi = {10.1021/acs.orglett.9b01158}

}

MLA

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MLA Copy

Li, Feng, et al. “Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C–H Methoxylation and Chlorination of Benzaldehydes.” Organic Letters, vol. 21, no. 10, May. 2019, pp. 3692-3695. https://doi.org/10.1021/acs.orglett.9b01158.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)

Profiles

Yirong Zhou