Functional Alkylstannanes

P-Hydroxyalkyltin compounds can be prepared by the reaction of a tin-metal bonded compound I-FSn0 M0+ (M = Li,79 Na,80 or MgBr,81) with an epoxide, for example equation 6-33 79 

A similar reaction with a 2-chloroalkylamine gives P-aminotin compounds 82 

The opposite polarity in the organotin reagent R3Sn5+X5 can be exploited in, for example, the reaction of a tin alkoxide with an vinyl ester,83 the addition of an alkoxy- or amino-tin compound to a ketene,84 the reaction of a silyl enolate with a tin chloride,85 or the addition of an alkyltin hydride under non-radical conditions to an a,P-unsaturated carbonyl compound.86 

The alkyltin bond can also be formed by the homolytic hydrostannation of a vinyl compound C=C-X, provided the group X is itself not subject to attack.87 

An alternative approach involves the insertion of a carbene unit from a diazoaliphatic 

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The stannylmetallic compounds R3SnLi or R3SnMgX give access to a variety of cr-functional alkylstannanes. They react with alkoxyalkyl halides to give a-alkoxyalkylstannanes, and a convenient one-pot method is shown in Equation (43).80... 

As expected, the bioactivities of alkylstannanes are a function only of steric effects and polarizability. 

Borylation of the benzylic position of arenes via C—H functionalization has been achieved. Yu has also reported the ability construct C-B bonds via directed C—H functionalization of arylbenzamides catalyzed by Pd(II). Formation of carbon-carbon bonds between arenes and alkyltrifluoroborates, alkylstannanes, and alkyl halides has been reported. The incorporation of amino acid derived... 

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