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  • Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation.

Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation.

Advanced synthesis & catalysis (2010-12-18)
Jason R Zbieg, Takeo Fukuzumi, Michael J Krische
ABSTRACT

Exposure of alcohols 1a-1i to butadiene in the presence of a cyclometallated iridium catalyzed derived from allyl acetate, 4-methoxy-3-nitrobenzoic acid and BIPHEP (2,2'-bis(diphenylphosphino)biphenyl) results in hydrogen transfer to generate aldehyde-allyliridium pairs, which engage in C-C coupling to form products of carbonyl crotylation. Under related conditions using 1,4-butanediol as hydrogen donor, butadiene reductively couples to aldehydes 2e-2g and 2i to furnish carbonyl crotylation products 3e-3g and 3i. Thus, butadiene mediated carbonyl crotylation occurs with equal facility from the alcohol or aldehyde oxidation level with complete levels of branched regioselectivity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-Methoxy-3-nitrobenzoic acid, 98%