Trichloromethylative Olefin Cycloamination by Photoredox Catalysis

The trichloromethyl group is an important functionality. It is a useful synthetic moiety and appears in the structures of natural and biologically active compounds; hence, developing synthetic methods for its introduction into structural motifs is an important objective. Herein, we report an efficie...

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Veröffentlicht in:European journal of organic chemistry 2021-08, Vol.2021 (32), p.4531-4535
Hauptverfasser: Harada, Shinji, Masuda, Ryuya, Morikawa, Takahiro, Nishida, Atsushi
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container_end_page 4535
container_issue 32
container_start_page 4531
container_title European journal of organic chemistry
container_volume 2021
creator Harada, Shinji
Masuda, Ryuya
Morikawa, Takahiro
Nishida, Atsushi
description The trichloromethyl group is an important functionality. It is a useful synthetic moiety and appears in the structures of natural and biologically active compounds; hence, developing synthetic methods for its introduction into structural motifs is an important objective. Herein, we report an efficient chemistry for the trichloromethylations and cycloaminations of olefin. These reactions are realized in a single step and triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond, with the resulting intermediate trapped through intramolecular reaction with an amino group. This process facilitates the construction of N‐heterocycles having trichloromethyl units and tetrasubstituted carbons from simple compounds under mild conditions. The trichloromethyl group is an important functionality as it appears in the structures of biologically active compounds. The trichloromethylative olefin cycloaminations are reported. These reactions are triggered by the addition of the trichloromethyl radical, generated from bromotrichloromethane by photoredox catalysis, to a double bond. This process facilitates the construction of N‐heterocycles having trichloromethyl units.
doi_str_mv 10.1002/ejoc.202100898
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subjects Alkenes
Catalysis
Cyclization
Heterocycles
Photocatalysis
Photoredox catalysis
Trichloromethyl
title Trichloromethylative Olefin Cycloamination by Photoredox Catalysis
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