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Efficient and selective Stille cross-coupling of benzylic and allylic bromides using bromobis(triphenylphosphine)(N-succinimide)palladium(II)

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
3
Identifiers
DOI: 10.1016/j.tetlet.2003.11.014

Abstract

Abstract Allylic and benzylic bromides are cross-coupled with organostannanes efficiently using the precatalyst [Pd(NCOC 2H 4CO)(PPh 3) 2Br] 1 . Significantly, these reactions do not require the use of hexamethylphosphoramide (HMPA) as the solvent, or additional ligands, such as trifurylphosphine or triphenylarsine. Selectivity for benzyl bromide over bromobenzene is observed for precatalyst 1 , against the precatalysts, bromobis(triphenylphosphine)(benzyl)palladium(II) and bis(triphenylphosphine)palladium(II) bromide.

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