Biologically interesting fused oligocyclic lactams have been prepared via an intramolecular redox-neutral cyclization process. By the proper choice of the substrates with a wide variety of tethered olefins, the less favored C-H bond can be activated and functionalized. This C-H activation proceeds under mild conditions, obviates the need for external oxidants, and displays a broad scope with respect to the substituents.
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http://dx.doi.org/10.1039/c4cc00029c | DOI Listing |
Chem Sci
December 2024
School of Chemistry and Chemical Engineering, Hainan University Haikou 570228 China
Org Lett
October 2024
College of Chemistry and Materials Science, Jinan University, Guangzhou, Guangdong 511443, China.
A variety of polycyclic benzazepines were rapidly constructed by NHC-catalyzed regioselective redox-neutral intramolecular tandem cyclization. Initial mechanistic studies revealed that a SET radical process was possibly involved.
View Article and Find Full Text PDFOrg Lett
August 2024
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, U.P., India.
5,10-Dihydroindeno[1,2-]indole has served as an important starting precursor for BARAC-fluor reagent in medicinal chemistry. Herein, an unprecedented -TsOH assisted intramolecular C2-arylation of NH-indoles via C(sp)-CN/C(sp)-H coupling, offering a series of 5,10-dihydroindeno[1,2-]indoles with moderate to good yields, has been showcased under redox-neutral conditions. Furthermore, successful scalability and synthetic applications highlight the practical nature of the method.
View Article and Find Full Text PDFChem Commun (Camb)
January 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research, Berhampur 760010, India.
We, herein, report a Pd(0) and Brønsted acid-catalyzed redox-neutral intramolecular -allylation of indoles and pyrroles with alkynes for the synthesis of biologically important imidazolidinone-fused N-heterocycles. The allylation is completely atom-economical and is applicable to a wide range of substrates. The methodology eliminates the use of a leaving group or an oxidizing agent, often employed for the allylation of nucleophiles.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2023
Department of Chemistry, Indiana University, Bloomington, IN 47405, USA.
Despite the unique reactivity of vitamin B and its derivatives, B -dependent enzymes remain underutilized in biocatalysis. In this study, we repurposed the B -dependent transcription factor CarH to enable non-native radical cyclization reactions. An engineered variant of this enzyme, CarH*, catalyzes the formation γ- and δ-lactams through either redox-neutral or reductive ring closure with marked enhancement of reactivity and selectivity relative to the free B cofactor.
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