Journal article
Authors list: Fokin, AA; Schreiner, PR
Publication year: 2003
Pages: 1035-1052
Journal: Advanced Synthesis & Catalysis
Volume number: 345
Issue number: 9-10
ISSN: 1615-4150
DOI Link: https://doi.org/10.1002/adsc.200303049
Publisher: Wiley
Abstract:
The present overview of alkane functionalization reactions presents
comparisons between radical and metal‐initiated (sometimes
metal‐catalyzed) methodologies. While metal‐catalyzed processes are
excellent approaches to this problem, metal‐free alternatives are
equally if not, at least from an environmental and cost perspective,
more useful. This conclusion is supported by the fact that many
so‐called metal‐catalyzed reactions also work without the metal present,
and the large variety of metals showing the same product distributions
emphasizes that the metal often just aids in the generation of the
active species, i.e., the metal itself is not participating in
the crucial C-H activation step. Highly selective alkane
functionalization reactions such as those derived from nitroxyl and
related radicals as well as through radical reactions conducted in
phase‐transfer catalyzed systems are available but generally
underutilized. These systems, in contrast to typical metal‐catalyzed
approaches, are also applicable to highly strained alkanes and offer the
highest 3°/2° C-H selectivities reported to date in a radical reaction.
The article closes with representative experimental protocols for the
PTC bromination of cubane as an example of the applicability of this
method to strained hydrocarbons and the direct iodination of cyclohexane
as well as adamantane as typical alkanes bearing secondary and tertiary
C-H bonds.
Citation Styles
Harvard Citation style: Fokin, A. and Schreiner, P. (2003) Metal-free, selective alkane functionalizations, Advanced Synthesis & Catalysis, 345(9-10), pp. 1035-1052. https://doi.org/10.1002/adsc.200303049
APA Citation style: Fokin, A., & Schreiner, P. (2003). Metal-free, selective alkane functionalizations. Advanced Synthesis & Catalysis. 345(9-10), 1035-1052. https://doi.org/10.1002/adsc.200303049
