Alkanes arylation

Directing-Group Containing Arene and Alkane Arylation. 64... 

Palladium and copper-catalyzed arylation of C-H bonds by aryl halide reagents is reviewed. The emphasis of the review is on directing-group-containing arene and alkane arylation catalyzed by palladium and on sp2 C-H bond arylation catalyzed by copper. Literature up to early 2009 is covered. 

Lafrance M, Gorelsky SI, Fagnou K (2007) High-yielding palladium-catalyzed intramolecular alkane arylation reaction development and mechanistic studies. J Am Chem Soc 129 14570-14571... 

Alkanes, aryl- Alcohol+ketone 2-Methyl- Mo,V-Heteropoly- ... 

Alkanes, aryl- Alcohol+ketone 3-Methyl- Mfacac), 55k... 

Preparation of alkanes using lithium di alkylcuprates (Section 14 11) Two alkyl groups may be coupled together to form an alkane by the reaction of an alkyl hal ide with a lithium dialkylcuprate Both alkyl groups must be primary (or meth yl) Aryl and vinyl halides may be used in place of alkyl halides... 

The coupling of alkyl halides 1 upon treatment with a metal, e.g. elemental sodium, to yield symmetrical alkanes 2, is called the Wurtz reaction. Aryl alkanes can be prepared by the Wurtz-Fittig reaction, i.e. the coupling of aryl halides with alkyl halides. 

Dibrom-1 -aryl-alkane Cu2CIj 1-Aryl-alkene s. Bd. V/l b, S. 202... 

Wahrend Aryl-1,2-diketone in der Regel zu a-Hydroxy-ketonen reduziert werden, erhalt man aus Alkan-l,2-dionen auch die entsprechenden Glykole z. B. ... 

Alkane 101, 50-70, 397 103, 503, 522, 524, 5491, 564, 576, 623 aus Halogen-alkanen und Chrom(II)-perchlorat 511 Organo-silancn/Aluminiuinchlorid 392 durch reduktive Kupplung von Benzyl- und Allyl-halogcniden mit Titan(II)-Salzen 496 1-Aryl- 525... 

The reaction between alkyl halides and alkanediazotates (114) gives azoxy-alkanes. The R and R groups may be the same or different, but neither may be aryl or tertiary alkyl. The reaction is regioselective only the isomer shown is obtained. 

Haloalkynes (R—C=C—X) react with ArSnBu3 and Cul to give R—C= C—Ar. Acetylene reacts with two equivalents of iodobenzene, in the presence of a palladium catalyst and Cul, to give 1,2-diphenylethyne. 1-Trialkylsilyl alkynes react with 1-haloalkynes, in the presence of a CuCl catalyst, to give diynes and with aryl triflates to give 1-aryl alkynes. Alkynes couple with alkyl halides in the presence of Sml2/Sm. Alkynes react with hypervalent iodine compounds " and with reactive alkanes such as adamantane in the presence of AIBN. ... 

This section contains dehydrogenations to form alkenes and unsaturated ketones, esters and amides. It also includes the conversion of aromatic rings to alkenes. Reduction of aryls to dienes is found in Section 377 (Alkene-Alkene). Hydrogenation of aryls to alkanes and dehydrogenations to form aryls are included in Section 74 (Alkyls from Alkenes). 

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