New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis (in special issue on recent advances in organotin chemistry)

Hernán, Alejandro G., Horton, Peter N., Hursthouse, Michael B. and Kilburn, Jeremy D. (2006) New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis (in special issue on recent advances in organotin chemistry). Journal of Organometallic Chemistry, 691 (8), 1466-1475. (doi:10.1016/j.jorganchem.2005.11.031).

Abstract

Novel resin-bound organotin reagents have been prepared, including for the first time resin-bound dimethyl tin reagents. Mild methodology has also been developed for the very efficient synthesis of resin-bound distannanes. The resin-bound tin chloride reagents have been used in a catalytic Stille coupling cycle and the resin-bound distannanes have been used in atom transfer cyclisations and proved to be much more effective than previously described resin-bound distannanes. As expected the use of resin-bound tin reagents facilitated their easy removal at the end of the reaction, and consequently residual tin levels in the organic products were low or negligible. The resin-bound distannanes Could not, however, be successfully used for the palladium catalysed stannylation of a simple aryl iodide, which would have provided a useful approach to radiolabeling of aromatic substrates. The reasons for the failure in the stannylation process is unclear but crystal structure evidence indicates that there is a hypervalent interaction between the resin-bound tin atom and an adjacent ether oxygen which may effect the reactivity of the tin intermediates in the stannylation sequence.

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Contributors

Author: Peter N. Horton

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