Metal-free halogenation of arylboronate with N-halosuccinimide

Kamei, Toshiyuki; Ishibashi, Aoi; Shimada, Toyoshi

doi:10.1016/j.tetlet.2014.06.003

Cited by 17 publications

(7 citation statements)

References 26 publications

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“…Applying an adapted protocol from Kamei and co-workers allowed to introduce a bromine as third functional group. 20 Treating 8 at low temperature with NBS in DMF provided the brominated compound 9 in excellent 93% isolated yield after column chromatography (CC) as brown oil. The combination of the strong para -directing amino group and the ortho -directing boronic acid substituent result in perfect regiocontrol of the bromination reaction reflected in the excellent yield of 9 .…”

Section: Resultsmentioning

confidence: 99%

Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

et al. 2018

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Section: Resultsmentioning

confidence: 99%

Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

et al. 2018

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“…Afterwards, Miyaura-borylation was performed to react 11 with bis(pinacolato)diboron (B 2 pin 2 ) in the presence of PdCl 2 (dppf) and KOAc as a catalyst and base, respectively, providing boronate ester 12 in a good yield of 81%. Finally, the chlorination of 12 ortho to the boronate ester by means of N -chloro-succinimide (NCS) in DMF at room temperature afforded 9c in a yield of 56% [38].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and In Vitro Evaluation of 8-Pyridinyl-Substituted Benzo[e]imidazo[2,1-c][1,2,4]triazines as Phosphodiesterase 2A Inhibitors

et al. 2019

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Phosphodiesterase 2A (PDE2A) is highly expressed in distinct areas of the brain, which are known to be related to neuropsychiatric diseases. The development of suitable PDE2A tracers for Positron Emission Tomography (PET) would permit the in vivo imaging of the PDE2A and evaluation of disease-mediated alterations of its expression. A series of novel fluorinated PDE2A inhibitors on the basis of a Benzoimidazotriazine (BIT) scaffold was prepared leading to a prospective inhibitor for further development of a PDE2A PET imaging agent. BIT derivatives (BIT1–9) were obtained by a seven-step synthesis route, and their inhibitory potency towards PDE2A and selectivity over other PDEs were evaluated. BIT1 demonstrated much higher inhibition than other BIT derivatives (82.9% inhibition of PDE2A at 10 nM). BIT1 displayed an IC50 for PDE2A of 3.33 nM with 16-fold selectivity over PDE10A. This finding revealed that a derivative bearing both a 2-fluoro-pyridin-4-yl and 2-chloro-5-methoxy-phenyl unit at the 8- and 1-position, respectively, appeared to be the most potent inhibitor. In vitro studies of BIT1 using mouse liver microsomes (MLM) disclosed BIT1 as a suitable ligand for 18F-labeling. Nevertheless, future in vivo metabolism studies are required.

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“…Kamei et al . in 2014 [71] provided another efficient halogenation methodology in furan, thiophene and also in similar system taking different pinacol boronate substrates (Scheme 60). The protocol was also extendable to some arenes as well.…”

Section: Transition Metal‐free C(sp2)−h Bond Halogenation In Heteroar...mentioning

confidence: 99%

“…Pyridine systems (71) have been chlorinated very effectively under transition metal-free condition using SOCl 2 as the chlorine source in presence of base in DCM medium. [59] Very large and complicated molecules have undergone the chlorination reaction with excellent yields(Scheme 48).…”

Section: Chlorinationmentioning

confidence: 99%

“…Presence of strong electron withdrawing groups in rings such as thiophene and deactivated rings such as furan and thiazoles showed less reactivity or no reactivity at all. [70] Kameiet al in 2014 [71] provided another efficient halogenation methodology in furan, thiophene and also in similar system taking different pinacol boronate substrates (Scheme 60). The protocol was also extendable to some arenes as well.…”

Section: General Halogenation On Heteroarene Systems Using Different ...mentioning

confidence: 99%

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Recent Update on Transition Metal‐Free C(sp²)−H Bond Halogenation in (Hetero) Arenes

2021

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Halogen incorporated arenes and heteroarenes are often used as useful intermediates as well as target products in organic synthesis. Often, CÀ H bond halogenation is attempted using transition metals (Pd, Cu, Au, Rh etc.). However, keeping the environmental concerns in mind, transition metal free protocols are more relevant and essential in recent times. In this context, improvised methods are widely being developed to evade transition metals. A great deal of work has been done on this topic in recent times and still going on. The intention of this review is to cover recent works on transition metal-free C(sp 2 )À H bond halogenations on arenes as well as heteroarenes.

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Metal-free halogenation of arylboronate with N-halosuccinimide

Cited by 17 publications

References 26 publications

Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

Synthesis and In Vitro Evaluation of 8-Pyridinyl-Substituted Benzo[e]imidazo[2,1-c][1,2,4]triazines as Phosphodiesterase 2A Inhibitors

Recent Update on Transition Metal‐Free C(sp²)−H Bond Halogenation in (Hetero) Arenes

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Metal-free halogenation of arylboronate with N-halosuccinimide

Cited by 17 publications

References 26 publications

Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

Molecular dynamic staircases: all-carbon axial chiral “Geländer” structures

Synthesis and In Vitro Evaluation of 8-Pyridinyl-Substituted Benzo[e]imidazo[2,1-c][1,2,4]triazines as Phosphodiesterase 2A Inhibitors

Recent Update on Transition Metal‐Free C(sp2)−H Bond Halogenation in (Hetero) Arenes

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Recent Update on Transition Metal‐Free C(sp²)−H Bond Halogenation in (Hetero) Arenes