, volume 85 , issue 2 , pages 1009-1021

Palladium-Catalyzed C–H/C–H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1H-Indazoles

Jingbo Yu ¹

Xinjie Yang ¹

Chongyang Wu ¹

Weike Su ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

National Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P.R. China |

Publication type: Journal Article

Publication date: 2019-12-11

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.9b02951

Copy DOI

PubMed ID: 31822061

Organic Chemistry

Abstract

C3-alkenylated and C3-(hetero)arylated 1H-indazoles are privileged structural motifs in numerous pharmaceuticals. Direct C3-alkenylation and C3-(hetero)arylation of 1H-indazoles have been significantly challenging because of the inert nature of this carbon center. Herein, we present an efficient mechanochemical strategy for palladium-catalyzed C-H/C-H cross-coupling to construct C3-alkenylated and C3-heteroarylated 1H-indazoles using low-cost copper oxidants with satisfactory product yields and broad functional group tolerance. The robustness of the developed protocols was further demonstrated by the unprecedented total mechanosynthesis of the intermediate of PLK4 inhibitor CFI-400945 and HIF-1α inhibitor YC-1.

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Zappimbulso Nicola

4 publications, 92 citations

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Yu J. et al. Palladium-Catalyzed C–H/C–H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1H-Indazoles // Journal of Organic Chemistry. 2019. Vol. 85. No. 2. pp. 1009-1021.

GOST all authors (up to 50) Copy

Yu J., Yang X., Wu C., Su W. Palladium-Catalyzed C–H/C–H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1H-Indazoles // Journal of Organic Chemistry. 2019. Vol. 85. No. 2. pp. 1009-1021.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.joc.9b02951

UR - https://doi.org/10.1021/acs.joc.9b02951

TI - Palladium-Catalyzed C–H/C–H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1H-Indazoles

T2 - Journal of Organic Chemistry

AU - Yu, Jingbo

AU - Yang, Xinjie

AU - Wu, Chongyang

AU - Su, Weike

PY - 2019

DA - 2019/12/11

PB - American Chemical Society (ACS)

SP - 1009-1021

IS - 2

VL - 85

PMID - 31822061

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2019_Yu,

author = {Jingbo Yu and Xinjie Yang and Chongyang Wu and Weike Su},

title = {Palladium-Catalyzed C–H/C–H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1H-Indazoles},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {85},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/acs.joc.9b02951},

number = {2},

pages = {1009--1021},

doi = {10.1021/acs.joc.9b02951}

}

MLA

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MLA Copy

Yu., Jingbo, et al. “Palladium-Catalyzed C–H/C–H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1H-Indazoles.” Journal of Organic Chemistry, vol. 85, no. 2, Dec. 2019, pp. 1009-1021. https://doi.org/10.1021/acs.joc.9b02951.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)