4.5 Article

Buchwald-Hartwig Amination, High-Throughput Experimentation, and Process Chemistry: An Introduction via Undergraduate Laboratory Experimentation

Journal

JOURNAL OF CHEMICAL EDUCATION
Volume 98, Issue 3, Pages 996-1000

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jchemed.0c01355

Keywords

Upper-Division Undergraduate; Laboratory Instruction; Organic Chemistry; Hands-On Learning/Manipulatives; Inquiry-Based/Discovery Learning; Problem Solving/Decision Making; Amines/Ammonium Compounds; Applications of Chemistry; Catalysis; Coordination Compounds; Drugs/Pharmaceuticals; Industrial Chemistry; Organometallics; Synthesis

Funding

  1. Salisbury University's Henson School of Science and Technology
  2. Henson School of Science and Technology
  3. National Science Foundation [MRI-1827905]

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This three-part laboratory experiment explores key aspects of the Buchwald-Hartwig amination cross-coupling reaction through guided-inquiry learning strategies, including high-throughput experimentation techniques, result evaluation, preparative-scale reaction setup, and full characterization of target molecules. This experiment serves as the final experiment in the fourth-year undergraduate chemistry curriculum, providing students with a capstone learning experience.
This three-part laboratory experiment investigates key aspects of the Buchwald-Hartwig amination cross-coupling reaction through guided-inquiry learning strategies. The first part of this experiment utilizes high-throughput experimentation techniques to reinforce, explore, and extend fundamental concepts that are represented in the classroom, including the use of air-free Schlenk techniques and heteronuclear NMR analysis. The second component challenges students to evaluate their results to design, set up, and perform a preparative-scale Buchwald-Hartwig amination. Finally, students purify and isolate their products using column chromatography allowing them to fully characterize their target molecules through a variety of analytical techniques. This experiment represents one of the final experiments performed in the fourth-year undergraduate chemistry curriculum and serves as a capstone learning experience for students.

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