Journal
SYNLETT
Volume -, Issue 7, Pages 1077-1080Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0028-1088222
Keywords
niobium pentachloride; niobium pentabromide; alkyl halides; halogenation; rearrangements
Categories
Funding
- National Institutes of Health [2R15A1051352-03]
- National Science Foundation [0808996, 0421252, 0614785]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0421252, 0808996] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0614785] Funding Source: National Science Foundation
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Sequential addition of vinylmagnesium bromide and NbCl5, or NbBr5, to a series of aldehydes and ketones directly provides homologated, allylic halides. Transposition of the intermediate vinyl alkoxide is envisaged through a metalo-halo-[3,3] rearrangement with concomitant delivery of the halogen to the terminal carbon. The [3,3] rearrangement is equally effective for the conversion of a propargyllic alcohol to the corresponding allenyl bromide.
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