Construction of N-Alkyl- and N-Arylaziridines from Unprotected Amines via C-H Oxidative Amination Strategy

Yang Yu; Meijuan Li; Yong Zhang; Yonghai Liu; Lei Shi; Wei Wang; Hao Li

doi:10.1021/acs.orglett.8b03799

Construction of N-Alkyl- and N-Arylaziridines from Unprotected Amines via C-H Oxidative Amination Strategy

Yang Yu, Meijuan Li, Yong Zhang, Yonghai Liu, Lei Shi, Wei Wang, Hao Li

Pharmacology and Toxicology

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

9 Scopus citations

Abstract

A copper-promoted intramolecular C-H oxidative amination reaction between secondary amine (N-H) and C(sp ³ )-H at the benzylic position of azaarenes or α-position of ketones for the synthesis of aziridine derivatives has been developed. Moreover, a practical annulation of electron-deficient vinylarenes with an unprotected primary alkyl amine by a Yb(OTf) ₃ -CuI relay system has also been reported. The reactions were carried out with oxygen as the sole oxidant to give the N-alkyl- and N-arylaziridines in good yields.

Original language	English (US)
Pages (from-to)	904-907
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.8b03799
State	Published - Feb 15 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b03799

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title = "Construction of N-Alkyl- and N-Arylaziridines from Unprotected Amines via C-H Oxidative Amination Strategy",

abstract = " A copper-promoted intramolecular C-H oxidative amination reaction between secondary amine (N-H) and C(sp 3 )-H at the benzylic position of azaarenes or α-position of ketones for the synthesis of aziridine derivatives has been developed. Moreover, a practical annulation of electron-deficient vinylarenes with an unprotected primary alkyl amine by a Yb(OTf) 3 -CuI relay system has also been reported. The reactions were carried out with oxygen as the sole oxidant to give the N-alkyl- and N-arylaziridines in good yields.",

author = "Yang Yu and Meijuan Li and Yong Zhang and Yonghai Liu and Lei Shi and Wei Wang and Hao Li",

note = "Funding Information: This work was supported by the National Natural Science Foundation of China (21572054, 21572055, and 21738002), the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the Fundamental Research Funds for the Central Universities, and the China 111 Project (Grant B07023). Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b03799",

language = "English (US)",

volume = "21",

pages = "904--907",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Construction of N-Alkyl- and N-Arylaziridines from Unprotected Amines via C-H Oxidative Amination Strategy

AU - Yu, Yang

AU - Li, Meijuan

AU - Zhang, Yong

AU - Liu, Yonghai

AU - Shi, Lei

AU - Wang, Wei

AU - Li, Hao

N1 - Funding Information: This work was supported by the National Natural Science Foundation of China (21572054, 21572055, and 21738002), the program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the Fundamental Research Funds for the Central Universities, and the China 111 Project (Grant B07023). Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/2/15

Y1 - 2019/2/15

N2 - A copper-promoted intramolecular C-H oxidative amination reaction between secondary amine (N-H) and C(sp 3 )-H at the benzylic position of azaarenes or α-position of ketones for the synthesis of aziridine derivatives has been developed. Moreover, a practical annulation of electron-deficient vinylarenes with an unprotected primary alkyl amine by a Yb(OTf) 3 -CuI relay system has also been reported. The reactions were carried out with oxygen as the sole oxidant to give the N-alkyl- and N-arylaziridines in good yields.

AB - A copper-promoted intramolecular C-H oxidative amination reaction between secondary amine (N-H) and C(sp 3 )-H at the benzylic position of azaarenes or α-position of ketones for the synthesis of aziridine derivatives has been developed. Moreover, a practical annulation of electron-deficient vinylarenes with an unprotected primary alkyl amine by a Yb(OTf) 3 -CuI relay system has also been reported. The reactions were carried out with oxygen as the sole oxidant to give the N-alkyl- and N-arylaziridines in good yields.

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Construction of N-Alkyl- and N-Arylaziridines from Unprotected Amines via C-H Oxidative Amination Strategy

Abstract

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CCDC 1867799: Experimental Crystal Structure Determination

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Construction of N-Alkyl- and N-Arylaziridines from Unprotected Amines via C-H Oxidative Amination Strategy

Abstract

ASJC Scopus subject areas

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CCDC 1867799: Experimental Crystal Structure Determination

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