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

Autor:	Xu Cheng, Tao Ye, Shouyun Yu, Jie Dai, Dadong Lu
Rok vydání:	2019
Předmět:	chemistry.chemical_classification General Chemistry Bond formation Aldehyde Combinatorial chemistry Coupling reaction Education Catalysis chemistry.chemical_compound chemistry Transition metal Reagent Electrophile Organic synthesis
Zdroj:	Journal of Chemical Education. 96:2672-2675
ISSN:	1938-1328 0021-9584
DOI:	10.1021/acs.jchemed.9b00191
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4ac437dd06a776c23b61cde8fc2b05e9 https://doi.org/10.1021/acs.jchemed.9b00191 Zobrazit plný text záznamu