Palladium-catalyzed addition of arylboronic acids to isocyanates

Kianmehr, Ebrahim; Rajabi, Azam; Ghanbari, Mohammad

doi:10.1016/j.tetlet.2009.01.054

Cited by 23 publications

(3 citation statements)

References 51 publications

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“…Following up Murakami′s work, Kianmehr and co‐workers reported the Pd‐catalyzed cross‐coupling of arylboronic esters and aromatic isocyanates . Although both electron‐rich and electron‐poor boronic acids could be used, only moderate yields were consistently obtained, due to the unavoidable formation of biaryls through homocoupling.…”

Section: Metal‐catalyzed Amide Formation With Isocyanates As Couplmentioning

confidence: 99%

Forging Amides Through Metal‐Catalyzed C–C Coupling with Isocyanates

Serrano

Martı́n

2018

Eur J Org Chem

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The natural occurrence of amides and their unique roles in synthetic materials and biologically active compounds make amide synthesis one of the most routinely performed reactions in organic chemistry. Despite the advances achieved, there is a growing need for the design of new catalytic technologies to complement existing amide bond‐forming reactions, which are often based on the formation of carbon–nitrogen bonds. Recent years have witnessed the development of a new disconnection approach to forging amides by means of metal‐catalyzed carbon–carbon bond‐forming reactions. This microreview highlights the most recent developments in the use of isocyanates in metal‐catalyzed amidations that take place according to this design principle. With the aim of illustrating the prospective impact of the use of isocyanates as amide synthons, this review highlights the advantages and drawbacks of the existing methods and describes the mechanistic implications when appropriate.

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Section: Metal‐catalyzed Amide Formation With Isocyanates As Couplmentioning

confidence: 99%

Forging Amides Through Metal‐Catalyzed C–C Coupling with Isocyanates

Serrano

Martı́n

2018

Eur J Org Chem

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“…As part of our current studies on the development of efficient methods for the preparation of biologically active compounds (36)(37)(38)(39)(40)(41)(42)(43)(44), in this paper, Fe 3 O 4 @SiO 2 @ADMPT/H 6 P 2 W 18 O 62 as a new inorganic-organic hybrid nanocatalyst was prepared, characterized, and used as an effective catalyst in the synthesis of 1,4-DHPs 4 via one-pot reaction of various aromatic aldehydes 1, ethyl acetoacetate 2, and ammonium acetate 3 with good to high yield in ethanol (Scheme 1). To the best of our knowledge, there are no examples of the use of WD HPAs as the catalyst for the synthesis of 1,4-DHP derivatives.…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄@SiO₂@ADMPT/H₆P₂W₁₈O₆₂: a novel Wells–Dawson heteropolyacid-based magnetic inorganic–organic nanohybrid material as potent Lewis acid catalyst for the efficient synthesis of 1,4-dihydopyridines

Ghanbari

Moradi

Setoodehkhah

2018

Green Chemistry Letters and Reviews

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A novel Wells-Dawson heteropolyacid-based magnetic Inorganic-organic nanohybrid, Fe 3 O 4 @SiO 2 @ADMPT/H 6 P 2 W 18 O 62 , was fabricated and used as a green, efficient, eco-friendly, and highly recyclable catalyst for the one-pot and multi-component synthesis of 1,4-Dihydopyridine (1,4-DHP) derivatives from the reaction of various aromatic aldehydes with ethyl acetoacetate and ammonium acetate with good to excellent yields and in a short span of time. The nanohybrid catalyst was prepared by the chemical anchoring of Wells-Dawson heteropolyacid H 6 P 2 W 18 O 62 onto the surface of functionalized Fe 3 O 4 nanoparticles with 2,4-bis(3,5dimethylpyrazol)-triazine (ADMPT) linker. These nanocatalysts were identified by using scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), infrared spectroscopy (IR) and vibrating sample magnetometer (VSM). This protocol is developed as a safe, cost-effective and convenient alternate method for the synthesis of 1,4-DHP derivatives utilizing an eco-friendly, and a highly reusable catalyst.

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“…In modern organic chemistry, both tandem reactions and C-H functionalization are considered as efficient tools for the synthesis of complex molecules in terms of atom economy. As part of our ongoing research program on the development of efficient methods in organic synthesis and on the preparation of heterocyclic compounds [41][42][43][44][45][46], to develop a more atom economical and direct …”

Section: Introductionmentioning

confidence: 99%