Brønsted Acid-Catalyzed Hydroamination of N-Heterocycles to Unactivated Alkenes

Guanzheng Feng; Yisan Shen; Chenghui Sun; Weixiao Ji; He Huang; Siping Pang

doi:10.1002/ajoc.202500579

Brønsted Acid-Catalyzed Hydroamination of N-Heterocycles to Unactivated Alkenes

Guanzheng Feng, Yisan Shen, Chenghui Sun, Weixiao Ji^*, He Huang^*, Siping Pang^*

^*Corresponding author for this work

Beijing Institute of Technology

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

Abstract

A Brønsted acid-catalyzed hydroamination of unactivated olefins has been developed, enabling the efficient Markovnikov addition of nitrogen heterocycles to olefins. This reaction utilizes a catalytic amount of trifluoroacetic acid (TFA) to produce a diverse array of N-alkyl nitrogen heterocycles. The method is highly scalable, allowing for multigram synthesis, and a novel proton transfer species implicated in olefin activation has been identified.

Original language	English
Journal	Asian Journal of Organic Chemistry
DOIs	http://doi.org/10.1002/ajoc.202500579
Publication status	Accepted/In press - 2025
Externally published	Yes

Keywords

Acid catalysis
Markovnikov addition
Metal-free
N-heterocycles
Unactivated alkenes

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10.1002/ajoc.202500579

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title = "Br{\o}nsted Acid-Catalyzed Hydroamination of N-Heterocycles to Unactivated Alkenes",

abstract = "A Br{\o}nsted acid-catalyzed hydroamination of unactivated olefins has been developed, enabling the efficient Markovnikov addition of nitrogen heterocycles to olefins. This reaction utilizes a catalytic amount of trifluoroacetic acid (TFA) to produce a diverse array of N-alkyl nitrogen heterocycles. The method is highly scalable, allowing for multigram synthesis, and a novel proton transfer species implicated in olefin activation has been identified.",

keywords = "Acid catalysis, Markovnikov addition, Metal-free, N-heterocycles, Unactivated alkenes",

author = "Guanzheng Feng and Yisan Shen and Chenghui Sun and Weixiao Ji and He Huang and Siping Pang",

note = "Publisher Copyright: {\textcopyright} 2025 Wiley-VCH GmbH.",

year = "2025",

doi = "10.1002/ajoc.202500579",

language = "English",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "Wiley - VCH Verlag GmbH \& CO. KGaA",

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TY - JOUR

T1 - Brønsted Acid-Catalyzed Hydroamination of N-Heterocycles to Unactivated Alkenes

AU - Feng, Guanzheng

AU - Shen, Yisan

AU - Sun, Chenghui

AU - Ji, Weixiao

AU - Huang, He

AU - Pang, Siping

PY - 2025

Y1 - 2025

N2 - A Brønsted acid-catalyzed hydroamination of unactivated olefins has been developed, enabling the efficient Markovnikov addition of nitrogen heterocycles to olefins. This reaction utilizes a catalytic amount of trifluoroacetic acid (TFA) to produce a diverse array of N-alkyl nitrogen heterocycles. The method is highly scalable, allowing for multigram synthesis, and a novel proton transfer species implicated in olefin activation has been identified.

AB - A Brønsted acid-catalyzed hydroamination of unactivated olefins has been developed, enabling the efficient Markovnikov addition of nitrogen heterocycles to olefins. This reaction utilizes a catalytic amount of trifluoroacetic acid (TFA) to produce a diverse array of N-alkyl nitrogen heterocycles. The method is highly scalable, allowing for multigram synthesis, and a novel proton transfer species implicated in olefin activation has been identified.

KW - Acid catalysis

KW - Markovnikov addition

KW - Metal-free

KW - N-heterocycles

KW - Unactivated alkenes

UR - http://www.scopus.com/pages/publications/105011094541

U2 - 10.1002/ajoc.202500579

DO - 10.1002/ajoc.202500579

M3 - Article

AN - SCOPUS:105011094541

SN - 2193-5807

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

ER -

Brønsted Acid-Catalyzed Hydroamination of N-Heterocycles to Unactivated Alkenes

Abstract

Keywords

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