If CH Bonds Could Talk: Selective CH Bond Oxidation

• Published in: Angewandte Chemie International Edition Vol. 50; no. 15; pp. 3362 - 3374
• Main Authors: Newhouse, Timothy, Baran, Phil S.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 04.04.2011; WILEY‐VCH Verlag
• Subjects: Carbon - chemistry; CH activation; Hydrogen - chemistry; natural products; Oxidation-Reduction; synthesis design; synthetic methods
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201006368

CH oxidation has a long history and an ongoing presence in research at the forefront of chemistry and interrelated fields. As such, numerous highly useful articles and reviews have been written on this subject. Logically, these are generally written from the perspective of the scope and limitations of the reagents employed. This Minireview instead attempts to emphasize chemoselectivity imposed by the nature of the substrate. Consequently, many landmark discoveries in the field of CH oxidation are not discussed, but hopefully the perspective taken herein will allow CH oxidation reactions to be more readily incorporated into synthetic planning. Let the molecule do the talking: If CH bonds could talk, they would tell stories of inductive effects, conjugation, hyperconjugation, steric hindrance, and strain release. These stories are told from the perspective of synthetic planning and draw from the immense body of literature on the topic.