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Efficient two-step synthesis of 3-halo-3-enals or 2-halo-2-alkenyl ketones from propargylic bromides via a unique cationic 1,2-aryl or proton shift in electrophilic addition reaction of 2,3-allenols with X+

2005; Royal Society of Chemistry; Issue: 32 Linguagem: Inglês

10.1039/b508069j

1364-548X

Chunling Fu, Jing Li, Shengming Ma,

Catalytic Cross-Coupling Reactions

The reaction of readily available 1-substituted 2,3-allenols with Br2, NBS, or I2 afforded the not-easily-available but synthetically useful 3-halo-3-alkenals or 2-halo-2-alkenyl ketones in good yields via a sequential electrophilic interaction of X+ with the allene moiety , a 1,2-aryl or proton shift, and a H+-elimination process; the structures of the products were established by X-ray diffraction study.