Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross‐Coupling of Aryl Halides with Hydrazine Hydrate in Water

Siripuram, Vijay Kumar; Ma, Dawei

doi:10.1002/cjoc.201800326

Cited by 24 publications

(10 citation statements)

References 30 publications

(9 reference statements)

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“…For the synthesis of naphthalic anhydride hydrazine hydrochloride salt (NAHC), a previous method was adopted ( Kumar and Ma, 2018 ). A 10 ml resealable screwcap Schlenk tube equipped with a Teflon-coated magnetic stir bar was charged with CuI (9 mg, 8 mol%), BMPO (14 mg, 8 mol%), CTAB (25 mg, 16 mol%), 4-Bromo-1,8-naphthalic Anhydride (169 mg, 0.6 mmol), K 3 PO 4 (25 mg, 0.12 mmol, 0.2 equiv.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of naphthalimide-type chemsensor and its application in quality evaluation for polygonatum sibiricum Red

et al. 2022

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The premise and key of ensuring the safety and effectiveness of traditional Chinese medicine (TCM) is to construct appropriate quality evaluation system of TCM. This study aimed to establish a pre-column derivatization HPLC method for achieving the quality control of Polygonatum sibiricum by reacting synthesized 4-hydrazino-1,8-naphthalimide (HAN) with diverse monosaccharides from the hydrolytic product of P. sibiricum polysaccharides (PSPs), followed by HPLC separation. The HAN was synthesized based on a CuI-catalyzed cross-coupling reaction in water, and then employed as a novel chemosensor that reacts with reducing sugars. Good separation was achieved at a detection wavelength of 448 nm using an ZORBAX SB-C8 column under a gradient elution at a flow rate of 0.5 ml/min within 12 min. The monosaccharide compositions of PSP mainly include two hexoses [glucose (Glc), galactose (Gal)] and two hexuronic acids [glucuronic acid (GlcA) and galacturonic acid (GalA)], and the molar ratio of Glc, Gal, GlcA and GalA is 16.67:52.94:10.58:19.81. The verified HPLC method, possessing excellent precision and good accuracy, successfully achieved rapid qualitative and quantitative determination for PSP. Additionally, the HAN displayed fluorescence enhancement through “push–pull” mode, and fluorescence decreased through “pull–pull” mode after binding to monosaccharides, which is a potential for fluorescence determination of different monosaccharides.

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Section: Methodsmentioning

confidence: 99%

Synthesis of naphthalimide-type chemsensor and its application in quality evaluation for polygonatum sibiricum Red

et al. 2022

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“…In addition, 0.001 equiv of Cu 2 O/NFO ( L47 ) or MNFO ( L48 ) was found to be effective for the amination reaction of (hetero)aryl bromides at 80 °C or iodides at 60 °C, respectively (Table , entry 1) . Only 0.02 equiv of CuI/BMPO ( L36 ) was needed for catalyzing the reaction of aryl iodides and bromides with hydrazine hydrate (Table , entry 2) . With the modification of ligands, 0.01–0.02 equiv of Cu salts showed a powerful catalyzing effect in the coupling of (hetero)aryl iodides and bromides with other N -nucleophiles such as heteroanilines (Table , entry 3) and N -heterocycles (Table , entry 4), while 0.002–0.02 equiv of CuI/BPPO ( L35 ) or PPBO ( L46 ) was demonstrated to be effective for catalyzing diaryl ether synthesis (Table , entry 5) .…”

Section: Key Advances In Cu-mediated Ullmann-type Cross-coupling Reac...mentioning

confidence: 99%

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Yang

Zhao

2022

Org. Process Res. Dev.

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110

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Cu-mediated Ullmann-type cross-coupling has experienced significant advances over the last century since the seminal publication by Ullmann in 1901. These advances have significantly expanded the scope of the original classical Ullmann coupling of aryl halides for formation of diaryl compounds to include the formation of carbon−heteroatom and other carbon− carbon bonds. The introduction of bidentate ligands drastically improved the performance of this class of transformations to enable milder reaction conditions that can tolerate a wide range of sensitive functional groups. Recent development of more powerful second-generation bidentate ligands has further allowed the coupling of less reactive aryl chlorides to proceed smoothly and realized low catalyst and ligand loadings for a broad scope of Ullmann-type cross-coupling reactions. As a result of these breakthrough advances in the past decades, Cu-mediated Ullmann-type cross-coupling reactions have been frequently implemented in academic research and have found ubiquitous industrial applications including the preparation of pharmaceutical and agrochemical products. This review provides an overview of selected general Cu-mediated Ullmann-type transformations for the formation of carbon− carbon and carbon−heteroatom (C−N, C−O, C−S, and C−P) bonds and their applications in route design, process development, and scale-up of pharmaceutical and agrochemical processes.

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“…6 Alternative access to phenylhydrazines involves metal catalyzed cross coupling of phenyl halides. 7,8 Surprisingly, there are not many multicomponent reaction (MCR) approaches towards the assembly of the indole scaffold (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

Sustainable multicomponent indole synthesis with broad scope

et al. 2022

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Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross‐Coupling of Aryl Halides with Hydrazine Hydrate in Water

Cited by 24 publications

References 30 publications

Synthesis of naphthalimide-type chemsensor and its application in quality evaluation for polygonatum sibiricum Red

Synthesis of naphthalimide-type chemsensor and its application in quality evaluation for polygonatum sibiricum Red

Cu-Mediated Ullmann-Type Cross-Coupling and Industrial Applications in Route Design, Process Development, and Scale-up of Pharmaceutical and Agrochemical Processes

Sustainable multicomponent indole synthesis with broad scope

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