Enantioselective Transformation of Hydrazones via Remote NHC Catalysis: Activation Across C═N and N-N Bonds

Jiamiao Jin; Ya Lv; Wenli Tang; Kunpeng Teng; Yixian Huang; Jingxin Ding; Tingting Li; Guanjie Wang; Yonggui Robin Chi

doi:10.1021/acscatal.4c06029

Enantioselective Transformation of Hydrazones via Remote NHC Catalysis: Activation Across C═N and N-N Bonds

Jiamiao Jin, Ya Lv, Wenli Tang, Kunpeng Teng, Yixian Huang, Jingxin Ding, Tingting Li, Guanjie Wang^*, Yonggui Robin Chi^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The catalytic asymmetric transformation of nitrogen atoms to prepare heterocyclic molecules is of significant value in organic synthesis and biological applications. Here, we disclose the activation of the nitrogen atom in hydrazine-derived hydrazone via an N-heterocyclic carbene (NHC) organic catalyst for highly enantioselective formal cycloaddition reactions. The range of NHC catalysis extends across several (carbon and hetero) atoms and diverse chemical bonds (C═N and N-N bonds) to activate nitrogen atoms at remote sites with excellent reactivity and (stereo)selectivity control. Our strategy for nitrogen atom activation, along with the NHC-bound diaza-diene intermediate generated during the catalytic process, offers alternative solutions for organic synthesis.

Original language	English
Pages (from-to)	18378-18384
Number of pages	7
Journal	ACS Catalysis
DOIs	https://doi.org/10.1021/acscatal.4c06029
Publication status	Accepted/In press - 2024
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2024 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

chiral heterocyclic molecule
enantioselective transformation
hydrazones
N-heterocyclic carbene
nitrogen atom activation

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10.1021/acscatal.4c06029

Cite this

@article{12486ebda96640e9a14f129139983339,

title = "Enantioselective Transformation of Hydrazones via Remote NHC Catalysis: Activation Across C═N and N-N Bonds",

abstract = "The catalytic asymmetric transformation of nitrogen atoms to prepare heterocyclic molecules is of significant value in organic synthesis and biological applications. Here, we disclose the activation of the nitrogen atom in hydrazine-derived hydrazone via an N-heterocyclic carbene (NHC) organic catalyst for highly enantioselective formal cycloaddition reactions. The range of NHC catalysis extends across several (carbon and hetero) atoms and diverse chemical bonds (C═N and N-N bonds) to activate nitrogen atoms at remote sites with excellent reactivity and (stereo)selectivity control. Our strategy for nitrogen atom activation, along with the NHC-bound diaza-diene intermediate generated during the catalytic process, offers alternative solutions for organic synthesis.",

keywords = "chiral heterocyclic molecule, enantioselective transformation, hydrazones, N-heterocyclic carbene, nitrogen atom activation",

author = "Jiamiao Jin and Ya Lv and Wenli Tang and Kunpeng Teng and Yixian Huang and Jingxin Ding and Tingting Li and Guanjie Wang and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

doi = "10.1021/acscatal.4c06029",

language = "English",

pages = "18378--18384",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Enantioselective Transformation of Hydrazones via Remote NHC Catalysis

T2 - Activation Across C═N and N-N Bonds

AU - Jin, Jiamiao

AU - Lv, Ya

AU - Tang, Wenli

AU - Teng, Kunpeng

AU - Huang, Yixian

AU - Ding, Jingxin

AU - Li, Tingting

AU - Wang, Guanjie

AU - Chi, Yonggui Robin

PY - 2024

Y1 - 2024

N2 - The catalytic asymmetric transformation of nitrogen atoms to prepare heterocyclic molecules is of significant value in organic synthesis and biological applications. Here, we disclose the activation of the nitrogen atom in hydrazine-derived hydrazone via an N-heterocyclic carbene (NHC) organic catalyst for highly enantioselective formal cycloaddition reactions. The range of NHC catalysis extends across several (carbon and hetero) atoms and diverse chemical bonds (C═N and N-N bonds) to activate nitrogen atoms at remote sites with excellent reactivity and (stereo)selectivity control. Our strategy for nitrogen atom activation, along with the NHC-bound diaza-diene intermediate generated during the catalytic process, offers alternative solutions for organic synthesis.

AB - The catalytic asymmetric transformation of nitrogen atoms to prepare heterocyclic molecules is of significant value in organic synthesis and biological applications. Here, we disclose the activation of the nitrogen atom in hydrazine-derived hydrazone via an N-heterocyclic carbene (NHC) organic catalyst for highly enantioselective formal cycloaddition reactions. The range of NHC catalysis extends across several (carbon and hetero) atoms and diverse chemical bonds (C═N and N-N bonds) to activate nitrogen atoms at remote sites with excellent reactivity and (stereo)selectivity control. Our strategy for nitrogen atom activation, along with the NHC-bound diaza-diene intermediate generated during the catalytic process, offers alternative solutions for organic synthesis.

KW - chiral heterocyclic molecule

KW - enantioselective transformation

KW - hydrazones

KW - N-heterocyclic carbene

KW - nitrogen atom activation

UR - http://www.scopus.com/inward/record.url?scp=85210771429&partnerID=8YFLogxK

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U2 - 10.1021/acscatal.4c06029

DO - 10.1021/acscatal.4c06029

M3 - Article

AN - SCOPUS:85210771429

SN - 2155-5435

SP - 18378

EP - 18384

JO - ACS Catalysis

JF - ACS Catalysis

ER -

Enantioselective Transformation of Hydrazones via Remote NHC Catalysis: Activation Across C═N and N-N Bonds

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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