Solvent Effects on the Chemo- and Site-Selectivity of Transition Metal-Catalyzed Nitrene Transfer Reactions: Alternatives to Chlorinated Solvents

Transition metal-catalyzed, non-enzymatic nitrene transfer (NT) reactions to selectively transform C-H and C=C bonds to new C-N bonds are a powerful strategy to streamline the preparation of valuable amine building blocks. However, many catalysts for these reactions use environmentally unfriendly so...

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Published in:ChemSusChem 2024-01, Vol.17 (1), p.e202300964-e202300964
Main Authors: Ward, Robert M, Hu, Yun, Tu, Noah P, Schomaker, Jennifer M
Format: Article
Language:English
Subjects:
Benzene
Catalysts
Chemical reactions
Chloroform
Dichloroethane
Dichloromethane
Manganese
Metal phthalocyanines
Silver
Solvent effect
Solvents
Transition metals
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Hu, Yun
Tu, Noah P
Schomaker, Jennifer M
description Transition metal-catalyzed, non-enzymatic nitrene transfer (NT) reactions to selectively transform C-H and C=C bonds to new C-N bonds are a powerful strategy to streamline the preparation of valuable amine building blocks. However, many catalysts for these reactions use environmentally unfriendly solvents that include dichloromethane, chloroform, 1,2-dichloroethane and benzene. We developed a high-throughput experimentation (HTE) protocol for heterogeneous NT reaction mixtures to enable rapid screening of a broad range of solvents for this chemistry. Coupled with the American Chemical Society Pharmaceutical Roundtable (ACSPR) solvent tool, we identified several attractive replacements for chlorinated solvents. Selected catalysts for NT were compared and contrasted using our HTE protocol, including silver supported by N-dentate ligands, dinuclear Rh complexes and Fe/Mn phthalocyanine catalysts.
doi_str_mv 10.1002/cssc.202300964
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subjects Benzene
Catalysts
Chemical reactions
Chloroform
Dichloroethane
Dichloromethane
Manganese
Metal phthalocyanines
Silver
Solvent effect
Solvents
Transition metals
title Solvent Effects on the Chemo- and Site-Selectivity of Transition Metal-Catalyzed Nitrene Transfer Reactions: Alternatives to Chlorinated Solvents
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