Bystanding F+ Oxidants Enable Selective Reductive Elimination from High-Valent Metal Centers in Catalysis

✍ Scribed by Keary M. Engle; Tian-Sheng Mei; Dr. Xisheng Wang; Prof. Jin-Quan Yu

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 751 KB
• Volume: 50
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.201005142

✦ Synopsis

Abstract

Reductive elimination from partially or completely oxidized metal centers is a vital step in a myriad of carbon–carbon and carbon–heteroatom bond‐forming reactions. One strategy for promoting otherwise challenging reductive elimination reactions is to oxidize the metal center using a two‐electron oxidant (that is, from M^(n)^ to M^(n+2)^). However, many of the commonly used oxidants for this type of transformation contain oxygen, nitrogen, or halogen moieties that are subsequently capable of participating in reductive elimination, thus leading to a mixture of products. In this Minireview, we examine the use of bystanding F^+^ oxidants for addressing this widespread problem in organometallic chemistry and describe recent applications in Pd^II^/Pd^IV^ and Au^I^/Au^III^ catalysis. We then briefly discuss a rare example in which one‐electron oxidants have been shown to promote selective reductive elimination in palladium(II)‐catalyzed CH functionalization, which we view as a promising future direction in the field.