Green Oxidative Homocoupling of 1-Methylimidazole

Abstract

Relatively few experiments for the introductory organic chemistry laboratory demonstrate the utility of metal-catalyzed reactions in organic chemistry. A copper-catalyzed aerobic oxidative dimerization of 1-methylimidazole is described that introduces this topic. The reaction uses a low-cost substrate, a low-cost precatalyst that is stable to air and moisture, and a readily prepared base. The experiment can be performed using equipment found in a typical organic teaching lab. The crude product can be analyzed by 1 H NMR spectroscopy. The experiment allows for a general discussion of redox processes of organic substrates and green chemistry.

Exploring Green Chemistry with Aerobic Hypervalent Iodine Catalysis

“…While advances in the development of sustainable oxidation chemistry appear in the research literature, − there has thus far been a lack of reports in the chemical education literature that introduces undergraduate students to these emerging methods. , The experiment presented herein teaches students about sustainability and catalysis through the performance of both a Pd-catalyzed cross-coupling reaction and an aryl iodide-catalyzed aerobic C–N bond-forming reaction. Students compare the two reactions qualitatively (12 Principles of Green Chemistry) and quantitatively (green chemistry metrics pentagon).…”

“…Oxidation reactions are critical to organic chemistry, providing opportunities to introduce new functional groups, interconvert existing functional groups, and build molecular complexity. The demand for increasingly sustainable synthetic methods has motivated the development of a wide variety of new strategies for substrate oxidation. − The significant advances in sustainable oxidation chemistry that are evident in the research literature have not been reflected in the chemical education literature, which limits implementation of these new synthetic methods in the undergraduate teaching laboratory. , Given widespread recognition for the need to utilize more sustainable chemical processes, it is critical that students are both exposed to modern methods in sustainable synthesis and confront methods for the evaluation of the relative sustainability of disparate synthetic routes to a common product.…”

“…2−7 The significant advances in sustainable oxidation chemistry that are evident in the research literature have not been reflected in the chemical education literature, which limits implementation of these new synthetic methods in the undergraduate teaching laboratory. 8,9 Given widespread recognition for the need to utilize more sustainable chemical processes, it is critical that students are both exposed to modern methods in sustainable synthesis and confront methods for the evaluation of the relative sustainability of disparate synthetic routes to a common product.…”

A pesquisa em Ensino de Química Verde: temas e tipologias de estudos

“…O Cluster 3 aborda o esverdeamento de sínteses orgânicas, seja pelo uso de catalisadores metálicos; pelo uso de água como solvente; ativação por micro-ondas; ou condições ambiente de temperatura e pressão. Destacam-se as reações de acoplamento do tipo Suzuki-Miyaura, geralmente catalisadas por metais, realizadas com solvente aquoso ou com ativação por micro-ondas [53][54][55][56][57], de forma similar às reações de Wittig [58,59]. Procedimentos de metátese de olefinas e reações "click", procedimentos agraciados com o prêmio Nobel nos últimos anos, também são discutidos em versões verdes, sendo realizados em condições ambiente e solvente aquoso [60,61].…”

Engaging Students with the Real World in a Green Organic Chemistry Laboratory Group Project: A Presentation and Writing Assignment in a Laboratory Class

“…Several articles in this Journal have emphasized the significance of incorporating into the curriculum issues of green chemistry and environmental responsibility. − Many laboratory experiments on green chemistry have been reviewed in the book Green Organic Chemistry in Lectures and Laboratory . An increasing number continue to be developed. − …”