Regioselective Palladium-Catalyzed Buchwald–Hartwig Reaction of Arylhydrazines with Aryl Halides: Synthesis of <i>N</i> , <i>N</i> -Diarylhydrazines

An efficient regioselective palladium-catalyzed Buchwald-Hartwig reaction of arylhydrazines with aryl halides (including chlorides, bromides, and iodides) via C-N<sup>1</sup> bond formation has been successfully developed, providing a series of <i>N</i>,<i>N</i>-diarylhydrazines in moderate to excellent yields. This reaction features mild reaction conditions, the use of readily available substrates, a broad substrate scope, and a good compatibility with various functional groups. Furthermore, the total synthesis of an Ebola virus entry inhibitor was successfully achieved through a two-step process starting from the product <i>N</i>,<i>N</i>-diphenylhydrazine.

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Journal
The Journal of Organic Chemistry
Published
2025-12-24
DOI
https://doi.org/10.1021/acs.joc.5c02173
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Regioselective Palladium-Catalyzed Buchwald–Hartwig Reaction of Arylhydrazines with Aryl Halides: Synthesis of N , N -Diarylhydrazines

Shubing Shu, Z X Zhang, Xueyin Yao, Min Huang et al.
The Journal of Organic Chemistry
Catalytic Cross-Coupling Reactions
article

Regioselective Palladium-Catalyzed Buchwald–Hartwig Reaction of Arylhydrazines with Aryl Halides: Synthesis of N , N -Diarylhydrazines

Shubing Shu, Z X Zhang, Xueyin Yao, Min Huang, Zitong Huang, Junwei Peng, Meng Yu, Tao Wang
article en

Abstract

An efficient regioselective palladium-catalyzed Buchwald-Hartwig reaction of arylhydrazines with aryl halides (including chlorides, bromides, and iodides) via C-N<sup>1</sup> bond formation has been successfully developed, providing a series of <i>N</i>,<i>N</i>-diarylhydrazines in moderate to excellent yields. This reaction features mild reaction conditions, the use of readily available substrates, a broad substrate scope, and a good compatibility with various functional groups. Furthermore, the total synthesis of an Ebola virus entry inhibitor was successfully achieved through a two-step process starting from the product <i>N</i>,<i>N</i>-diphenylhydrazine.

The Journal of Organic ChemistryVol. 91(1)
BioMimetic Systems (United States) (US), Jiangxi Normal University (CN)
Openalex Percentile: Top 33%
Catalytic Cross-Coupling Reactions
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Regioselective Palladium-Catalyzed Buchwald–Hartwig Reaction of Arylhydrazines with Aryl Halides: Synthesis of <i>N</i> , <i>N</i> -Diarylhydrazines — Shubing Shu, Z X Zhang, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS