Alkanes heteroarenes

The Minisci reaction has successfully been applied for the alkylation of various heteroarenes, i. e. lepidine, pyrazine, quinoline and quinoxaline [2e, 2g, 10]. Organic compounds such as alkanes, alkenes, carboxylic acids, esters, amides, amines, alcohols, ethers, aldehydes, ketones, halides etc. have been successfully used as radical precursors in the Minisci reaction. A good overview of the different methods which have been applied to generate the alkyl radicals in these processes is summarized in [10b]. 

Appel D, Lutz-Wahl S, Fischer P, Schwaneberg U, Sehmid RD (2001) A P450 BM-3 mutant hydroxyl-ates alkanes, cycloalkanes, arenes and heteroarenes. J Bioteehnol 88 167-171... 

A number of systems have been developed for the functionalization of C-H bonds by their conversion into carbon-boron or carbon-silicon bonds. The substrates can be alkenes (Scheme 3.35), arenes (Schemes 3.36-3.38), heteroarenes (Schemes 3.39-3.41)" ° and even alkanes (Scheme 3.42)." With arenes, the electronic properties of the aromatic ring do not always seem to control the regioselectivity, as mixtures of isomers are often formed. Methyl-substituted aromatics may be borylated on the side chain depending on the choice of catalyst." ... 

Afterwards, Antonchick and coworkers [105] successfully extended this methodology to the oxidative cross coupling of heteroarenes and simple unfunctionalized alkanes (Scheme 40 (1)). The new C(sp )-C(sp ) bond formation occurred selectively at the electron-deficient site of the arene. The reaction was... 

---