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  • Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Journal of the American Chemical Society (2013-03-12)
Matthew S McCammant, Longyan Liao, Matthew S Sigman
ABSTRACT

A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1,3-Butadiene solution, 20 wt. % in toluene
Sigma-Aldrich
1,3-Butadiene solution, 15 wt. % in hexane
Sigma-Aldrich
1,3-Butadiene, ≥99%