Journal article

Publication year: 2004

Pages: 247-257

Journal: The Chemical Record

Volume number: 3

Issue number: 5

ISSN: 1527-8999

DOI Link: https://doi.org/10.1002/tcr.10070

Publisher: Wiley

Abstract: 
Alkane C-H-bond functionalization methods not utilizing metal-catalysis are discussed based on experimental and computational data, beginning with molecule-induced homolysis (reactions of alkanes with dioxiranes). Electrophilic reactions are elaborated next with an emphasis on mechanistic details that reveal that many so-called electrophilic C-H or C-C-bond insertions can be rationalized by electron-transfer reactions (inner sphere, H-coupled, and outer sphere). Finally, radical functionalizations utilizing carbon-centered (relatively stable) radicals generated under organocatalytic (phase-transfer catalysis, PTC) conditions are presented as valuable alternatives to other radical-chain alkane functionalizations. The remarkable chemo- and regioselectivities of these PTC radical reactions and the tolerance of high strain in certain aliphatic hydrocarbons make them particularly useful for laboratory-scale halogenations, in particular, iodinations of unactivated alkane C-H-bonds.

Harvard Citation style: Schreiner, P. and Fokin, A. (2004) Selective alkane C-H-bond functionalizations utilizing oxidative single-electron transfer and organocatalysis, The Chemical Record, 3(5), pp. 247-257. https://doi.org/10.1002/tcr.10070

APA Citation style: Schreiner, P., & Fokin, A. (2004). Selective alkane C-H-bond functionalizations utilizing oxidative single-electron transfer and organocatalysis. The Chemical Record. 3(5), 247-257. https://doi.org/10.1002/tcr.10070