Organic Letters 2018-04-09

Pd-Catalyzed Direct C–H Alkenylation and Allylation of Azine N-Oxides

Fares Roudesly, Luis F. Veiros, Julie Oble, Giovanni Poli

Index: 10.1021/acs.orglett.8b00689

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Abstract

A Pd-catalyzed direct C2-alkenylation of azine N-oxides with allyl acetate is disclosed. The products are formed through an allylation/isomerization cascade process. The use of a tri-tert-butylphosphonium salt as the ligand precursor and KF is mandatory for optimal yields. When cinnamyl acetate is used, the same catalytic system promotes C2-cinnamylation of the azine N-oxide without subsequent isomerization. A mechanism is proposed on the basis of experimental studies and DFT calculations.