3.8.4.3 C-C Cross-Coupling Reaction

Organochromium species are useful in coupling an aldehyde to an allylic moiety where the more substituted carbon of the allylic moiety attaches to the carbonyl carbon. The organochromium species is formed by the oxidative addition of Cr(II) to allylic halides. This reaction is known as Nozaki-Hiyama coupling reaction (Scheme 12).

Scheme 12

A further modification of the protocol allows the coupling of vinyl halides and vinyl tosylates with aldehydes. This is known as Nozaki-Takai-Hiyama-Kishi coupling where the formation of organochromium derivatives is promoted by catalytic amount of Ni(II) salts (Scheme 13). The stereochemistry of the vinyl group is retained in the product.

Scheme 13