Green Reductive Homocoupling of Bromobenzene

Abstract

b S Supporting Information T ransition-metal-mediated reactions have become a cornerstone of organic chemistry during recent decades. 1 These

Ligand-Free Suzuki–Miyaura Coupling Reactions Using an Inexpensive Aqueous Palladium Source: A Synthetic and Computational Exercise for the Undergraduate Organic Chemistry Laboratory

“…A similar approach to the introduction of transition metalcatalyzed couplings in the instructional laboratory has recently been described. 4 ■ SUMMARY An inexpensive and operationally simple procedure for introducing SMC reactions into a high-enrollment undergraduate organic chemistry laboratory course has been described. The reaction was effective for a range of commercially available aryl bromides and arylboronic acids.…”

“…The questions required students to identify various steps in a typical catalytic coupling cycle, recognize key reaction conditions, use the coupling reaction in a multistep synthesis, and predict the identity and detailed molecular structure of biaryl products. A similar approach to the introduction of transition metal-catalyzed couplings in the instructional laboratory has recently been described …”

“…The palladium-catalyzed coupling of organoboranes with organic halides in the presence of a base, termed the Suzuki–Miyaura coupling (SMC) reaction, is a fundamental method for the construction of C–C bonds. , The importance of this reaction and other Pd-catalyzed couplings was recognized by the award of the 2010 Nobel Prize in Chemistry to Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki . Introductory-level organic chemistry textbooks have only recently begun to include discussion of transition metal-catalyzed C–C bond forming reactions; in contrast, a number of instructional laboratory experiments focusing upon SMC reactions have been reported in the past decade . These procedures are excellent means by which to introduce such reactions into the undergraduate laboratory curriculum and are ideal for use in courses of relatively low enrollment.…”

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

“…Ballard has reported a green reductive homocoupling of bromobenzene to yield biphenyl (Scheme ). The method uses a relatively benign iron catalyst, iron­(III) acetylacetonate Fe­(acac) 3 (LD 50 = 1.87 g/kg, rat, oral), instead of more expensive and toxic palladium-based catalysts.…”

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. − …”