SYNTHESIS aryltrialkylstannanes

Dichloropyridine reacts in the dark (88% of disubstitution), whereas 2,6- and 3,5-dichloropyridines require photostimulation to afford ca. 80% yield of disubstitution products [26]. Aryltrialkylstannanes are valuable intermediates in organic synthesis, and the fact that they can be easily synthesized through the SRN1 mechanism, opens up important synthetic routes to different reaction schemes. For over a decade, the Pd(0)-catalyzed cross-coupling of organotin compounds with electrophiles, known as the Stille reaction, has been a very important tool in product design [104]. 

Much of the recent interest in the arylstannanes, particularly the aryltrialkylstannanes, however, derives from their use in the Stille reaction in which an aryl-C bond is generated by reaction with a halide or sulfonate RX, where R = vinyl, allyl, benzyl, or aryl, to give Ar-R under catalysis by palladium68 or another transition metal.69-72 The reactions are very tolerant of various functional groups, and are finding wide application in organic synthesis, and are considered in Section 22.2. 

Synthesis of aryltrialkylstannanes by reaction of aryl bromides with hexaalkyldistannanes Preparation of 2-nitrophenyltrimethylstannane (228) 199]... 

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