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

Keary M. Engle; Tian‐Sheng Mei; Xisheng Wang; Jin‐Quan Yu

doi:10.1002/anie.201005142

journal article Jan 24, 2011

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

Keary M. Engle

Tian‐Sheng Mei Xisheng Wang

Jin‐Quan Yu

Angewandte Chemie International Edition Vol. 50 No. 7 pp. 1478-1491 · Wiley

View at Publisher Save 10.1002/anie.201005142

Abstract

AbstractReductive 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 PdII/PdIV and AuI/AuIII 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.

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Citations

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Details

Published: Jan 24, 2011
Vol/Issue: 50(7)
Pages: 1478-1491
License: View

Authors

K

Keary M. Engle

Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States

Department of Biomedical Sciences, Oregon State University, Corvallis, Oregon, USA

J

Jin‐Quan Yu

Cite This Article

Keary M. Engle, Tian‐Sheng Mei, Xisheng Wang, et al. (2011). Bystanding F+ Oxidants Enable Selective Reductive Elimination from High‐Valent Metal Centers in Catalysis. Angewandte Chemie International Edition, 50(7), 1478-1491. https://doi.org/10.1002/anie.201005142

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

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