Molecules containing C-N bonds are of paramount importance in a diverse array of organic-based materials, natural products, pharmaceutical compounds, and agricultural chemicals. Biocatalytic C-N bond-forming reactions represent powerful strategies for producing these valuable targets, and their significance in the field of synthetic chemistry has steadily increased over the past decade. In this review, we provide a concise overview of recent advancements in the development of C-N bond-forming enzymes, with a particular emphasis on the inherent chemistry involved in these enzymatic processes. Overall, these enzymatic systems have proven their potential in addressing long-standing challenges in traditional small-molecule catalysis.
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http://dx.doi.org/10.1016/j.bioorg.2024.107108 | DOI Listing |
Nat Commun
January 2025
College of Chemistry, Central China Normal University (CCNU), Wuhan, Hubei, PR China.
C-C and C-X bond forming reactions are essential tools in organic synthesis, constantly revolutionizing human life. Among the key methods for constructing new chemical bonds are nucleophilic addition reactions involving imines. However, the inherent challenges in synthesizing and storing imines have stimulated interest in designing stable precursors, which generates imines in situ during the reaction.
View Article and Find Full Text PDFBeilstein J Org Chem
November 2024
Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico-Biológicas, Universidad Michoacana de San Nicolás de Hidalgo. Ciudad Universitaria, C.P. 58030, Morelia, Michoacán, Mexico.
A series of 1,5-disubstituted tetrazole-indole hybrids were synthesized via a high-order multicomponent reaction consisting of an Ugi-azide/Pd/Cu-catalyzed hetero-annulation cascade sequence. This operationally simple one-pot protocol allowed high bond-forming efficiency and creating six new bonds (two C-C, three C-N, and one N-N). Additionally, the products were evaluated against breast cancer MCF-7 cells, finding moderate activity in the compounds substituted with fluorine and chlorine.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
Organisch-Chemisches Institut, Universität Münster, Corrensstraße 36, 48149, Münster.
Despite the prominence of C-N bond forming cross-coupling reactions as a strategy to assemble molecular fragments, aminative coupling approaches, in which two fragments are assembled directly at the heteroatom, represents a rarely exploited retrosynthetic strategy. Herein, we report the design, synthesis, and implementation of an anomeric amide reagent capable of promoting highly regioselective aminative alkene-arene and alkene-alkene coupling reactions. This transformation follows a sequence of catalyst-free chloroamination, N-deprotection, and formal nitrene functionalization, all in one-pot.
View Article and Find Full Text PDFChemistry
November 2024
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377, München, Germany.
Chem Commun (Camb)
November 2024
KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia.
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