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2005
Dehalogenation
O 0236
(Bu3Sn)2—TBAF: A New Combination Reagent for the Reduction and Deuteraof Aryl Bromides and Iodides. — A combination of hexabutylditin and TBAF
03- 058 tion
or tributyltin hydride and TBAF reduces aromatic bromides and iodides under mild
conditions in near quantitative yield. Furthermore, this reagent combination allows the
deuteration of arenes by exchanging the residual water in TBAF for D2O. Limitations
associated with classical methods can be circumvented. For example, an aromatic
cis-alkene bromide is debrominated without reduction of the cis alkene. No products
derived from radical cyclization to the pendent arene are observed. Aromatic chlorides
and fluorides are inert to these reagent combinations. — (HARROWVEN*, D. C.;
GUY, I. L.; NUNN, M. I. T.; Chem. Commun. (Cambridge) 2004, 17, 1966-1967;
Dep. Chem., Univ. Southampton, Southampton SO17 1BJ, UK; Eng.) —
H. Hoennerscheid
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