Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms

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• 作者：Dr. Tian Qin ; Dr. Lara R. Malins ; Jacob T. Edwards ; Rohan R. Merchant ; Alexander J. E. Novak ; Jacob Z. Zhong ; Riley B. Mills ; Ming Yan ; Dr. Changxia Yuan ; Dr. Martin D. Eastgate and Prof. Phil S. Baran
• 刊名：Angewandte Chemie
• 出版年：2017
• 出版时间：January 2, 2017
• 年：2017
• 卷：129
• 期：1
• 页码：266-271
• 全文大小：4807K
• ISSN：1521-3757

文摘

Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiHb>3b>) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.