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Bystanding F + Oxidants Enable Selective Reductive Elimination from High‐Valent Metal Centers in Catalysis
Author(s) -
Engle Keary M.,
Mei TianSheng,
Wang Xisheng,
Yu JinQuan
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201005142
Subject(s) - reductive elimination , chemistry , catalysis , palladium , halogen , heteroatom , combinatorial chemistry , oxidative addition , metal , reductive dechlorination , carbon fibers , redox , organic chemistry , ring (chemistry) , materials science , biodegradation , alkyl , composite number , composite material
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 CH functionalization, which we view as a promising future direction in the field.