Decarbonylative cross coupling of phthalimides with diorganozinc reagents—Efforts toward catalysis

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• 作者：Kimberly S. DeGlopper ; Sarah K. Fodor ; Thomas B.D. Endean ; Jeffrey B. Johnson ; ^{jjohnson@hope.edu" class="auth_mail" title="E-mail the corresponding author}
• 关键词：CITOMGFGTPRDBS-UHFFFAOYSA-N ; USJLROKOUOOFFA-UHFFFAOYSA-N ; UYKCZIQILMZSBU-UHFFFAOYSA-N ; JHMPMXSSVYCSAU-UHFFFAOYSA-N ; HGSMTZHLRBZKDF-UHFFFAOYSA-N ; DDQCATFJRBPDGN-UHFFFAOYSA-N ; NSHNZBIQAZSVAI-UHFFFAOYSA-N
• 刊名：Polyhedron
• 出版年：2016
• 出版时间：16 August 2016
• 年：2016
• 卷：114
• 期：Complete
• 页码：393-398
• 全文大小：1089 K

文摘

The decarbonylative coupling of phthalimides with diorganozinc reagents to form o-substituted benzamides has been previously demonstrated as a viable process, but only with stoichiometric nickel(0). Investigations into a number of reaction variables, including solvent, ligand, and substrate substitution, have yielded multiple sets of conditions capable of achieving up to 10 catalyst turnovers, most successfully with the use of electron withdrawing nitrogen substituents on the phthalimide. In addition, these investigations have provided insight into the intermediates within the catalytic cycle and have revealed new approaches to the development of a general catalytic methodology.