Buchwald–Hartwig reaction: an update

Heravi, Majid M.; Zadsirjan, Vahideh; Malmir, Masoumeh; Mohammadi, Leila

doi:10.1007/s00706-021-02834-3

Cited by 17 publications

(6 citation statements)

References 207 publications

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“…- --------------------------------------------------------------Many reactions of redox-active metals achieve coupling of organic moieties in the presence of alkali metal tert-butoxides and other basic alkali metal salts. [1][2][3][4][5][6][7][8][9] In many instances, discussions about whether key steps involve organometallic intermediates or radical intermediates have arisen. This has led to the concept of hybrid organometallic/organic radical species.…”

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confidence: 99%

An Assay for Aryl Radicals Using BHAS Coupling

Murphy,

Clark,

Tyerman

et al. 2023

Preprint

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Aryl radicals are intermediates in many reactions, but determining their presence unambiguously is often challenging. As we recently reported, reaction of 2-iodo-1,3-dimethylbenzene 7 in benzene with KOtBu and a suitable organic additive, leads to a base-induced homolytic aromatic substitution (BHAS) coupling reaction giving 2,6-dimethylbiphenyl 12 and biphenyl 3 as coupled products, together with xylene. Biphenyl arises from a radical translocation and is the major coupling product. This paper now investigates that reaction, using deuterium isotope studies to provide detailed mechanistic support. The reaction gives very similar outcomes with two different radical generation sources, and in doing so, shows its ability to act as an assay for aryl radicals. An advantage of such a BHAS process is that it involves a chain reaction that can amplify radical activity.

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confidence: 99%

An Assay for Aryl Radicals Using BHAS Coupling

Murphy,

Clark,

Tyerman

et al. 2023

Preprint

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“…This is because both nitrogen atoms of intermediate 2 appeared to be equally active in the amide coupling reaction. Thus, good yields of both RU-75 and RU-184 were collected after stepwise nitro reduction and Buchwald–Hartwig amination [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

Computational Docking as a Tool in Guiding the Drug Design of Rutaecarpine Derivatives as Potential SARS-CoV-2 Inhibitors

Lin,

Wang,

Tang

et al. 2024

Molecules

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COVID-19 continues to spread around the world. This is mainly because new variants of the SARS-CoV-2 virus emerge due to genomic mutations, evade the immune system and result in the effectiveness of current therapeutics being reduced. We previously established a series of detection platforms, comprising computational docking analysis, S-protein-based ELISA, pseudovirus entry, and 3CL protease activity assays, which allow us to screen a large library of phytochemicals from natural products and to determine their potential in blocking the entry of SARS-CoV-2. In this new screen, rutaecarpine (an alkaloid from Evodia rutaecarpa) was identified as exhibiting anti-SARS-CoV-2 activity. Therefore, we conducted multiple rounds of structure-activity-relationship (SAR) studies around this phytochemical and generated several rutaecarpine analogs that were subjected to in vitro evaluations. Among these derivatives, RU-75 and RU-184 displayed remarkable inhibitory activity when tested in the 3CL protease assay, S-protein-based ELISA, and pseudovirus entry assay (for both wild-type and omicron variants), and they attenuated the inflammatory response induced by SARS-CoV-2. Interestingly, RU-75 and RU-184 both appeared to be more potent than rutaecarpine itself, and this suggests that they might be considered as lead candidates for future pharmacological elaboration.

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“…A wide range of reactions of redox-active metals achieve coupling of organic moieties and are brought about in the presence of alkali metal tert-butoxides and other basic alkali metal salts. [1][2][3][4][5][6][7][8][9] In many instances, discussions about whether key steps involve organometallic intermediates or radical intermediates have arisen. This has led to the concept of hybrid organometallic/organic radical species.…”

Section: Introductionmentioning

confidence: 99%