Anti‐Markovnikov Hydroamination of 2‐Vinylindoles With Pyrazole Catalyzed by 1,1′‐Binaphthyl‐2,2′‐Diyl Phosphate

The development of novel, efficient, and green synthetic methods for N ‐alkylpyrazoles represents an important objective in the realm of organic chemistry. This study presents the first 1,1′‐binaphthyl‐2,2′‐diyl hydrogenphosphate ( PA)‐ mediated anti‐Markovnikov addition of 2‐vinylindoles to diverse N ‐nucleophiles, including pyrazole, 2 H −1,2,3‐triazole, 1 H ‐indazole, and N ‐methylaniline. This mild protocol affords a variety of N ‐alkyl pyrazole scaffolds in moderate to good yields with good regioselectivity, demonstrating broad generality toward mono‐, di‐, and trisubstituted alkenes. Based on deuterium‐labeling and radical trapping experiments, a PA‐mediated 1,4‐addition ionic mechanism is proposed.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-02-24
DOI
https://doi.org/10.1002/ejoc.202501144
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Anti‐Markovnikov Hydroamination of 2‐Vinylindoles With Pyrazole Catalyzed by 1,1′‐Binaphthyl‐2,2′‐Diyl Phosphate

Tianhao Li, Chang Li, Jianwei Xie, M.‐W. TANG et al.
European Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Anti‐Markovnikov Hydroamination of 2‐Vinylindoles With Pyrazole Catalyzed by 1,1′‐Binaphthyl‐2,2′‐Diyl Phosphate

Tianhao Li, Chang Li, Jianwei Xie, M.‐W. TANG, Xianyan Jiao, Ping Liu, Jie Luo, Deping He
article en

Abstract

The development of novel, efficient, and green synthetic methods for N ‐alkylpyrazoles represents an important objective in the realm of organic chemistry. This study presents the first 1,1′‐binaphthyl‐2,2′‐diyl hydrogenphosphate ( PA)‐ mediated anti‐Markovnikov addition of 2‐vinylindoles to diverse N ‐nucleophiles, including pyrazole, 2 H −1,2,3‐triazole, 1 H ‐indazole, and N ‐methylaniline. This mild protocol affords a variety of N ‐alkyl pyrazole scaffolds in moderate to good yields with good regioselectivity, demonstrating broad generality toward mono‐, di‐, and trisubstituted alkenes. Based on deuterium‐labeling and radical trapping experiments, a PA‐mediated 1,4‐addition ionic mechanism is proposed.

European Journal of Organic ChemistryVol. 29(12)
Shihezi University (CN), Xinjiang University (CN)
Openalex Percentile: Top 28%
Catalytic C–H Functionalization Methods
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