ERIC Number: EJ1234641
Record Type: Journal
Publication Date: 2019-Nov
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Experimenting with a Suzuki-Miyaura Cross-Coupling Reaction That Demonstrates Tolerance toward Aldehyde Groups to Teach Undergraduate Students the Fundamentals of Transition-Metal-Catalyzed Reactions
Dai, Jie; Lu, Dadong; Ye, Tao; Yu, Shouyun; Cheng, Xu
Journal of Chemical Education, v96 n11 p2672-2675 Nov 2019
The Suzuki-Miyaura cross-coupling reaction, which is one of the most important methods for C-C bond formation in modern organic synthesis, exhibits broad functional group compatibility. A Suzuki-Miyaura cross-coupling protocol is reported that is suitable for demonstrating this compatibility in undergraduate laboratories. In this reaction, two unique features of boron reagents (tolerance toward water and electrophilic functional groups and reactivity toward transition metal complexes) are well reproduced. Nearly complete conversion of an aldehyde-bearing substrate occurs within 50 min, and the workup and purification procedures are convenient. The reaction was readily reproducible by second-year students in a first-semester undergraduate laboratory.
Descriptors: Science Instruction, Organic Chemistry, College Science, Hands on Science, Scientific Concepts, Concept Formation, Undergraduate Study, Science Laboratories, Water, Metallurgy
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A