Picolyl anions phenylation

The 2- and 4-picolyl anions are phenylated or mesitylated on reaction with chlorobenzene, phenyltri-methylammonium ion and 2-bromomesitylene under stimulation by light or potassium metal. The mechanism of reaction with bromobenzene and iodobenzene is not certain, with die aryne mechanism almost certainly intruding, and with iodobenzene some diarylation of the picolinyl anion results. The reaction of the 2-picolyl anion with 2-bromomesitylene, where an aryne process is impossible, is shown in equation (44). Similar reactions take place between the 4-picolyl anion and 2- or 4-bromopyridine or 2-chloro-quinoline.134... 

Phenylation of carbanions derived from olefins such as 1,3-pentadiene and l-(p-anisyl) propene and aromatics such as indene and fluorene are possible by the SrnI route in ammonia solvent. From the 1,3-pentadiene a mixture of mono-olefins and dienes is produced along with a small amount of di- and triphenylated material. Hydrogenation of the mixture gives 1-phenylpentane in 74% yield.106) Phenylation of 2- and 4-picolyl anions is conveniently effected in ammonia. When bromo- or iodobenzene is used for this purpose, reaction probably occurs by both SrnI and benzyne routes.111)... 

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