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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy
Chaolumen Bai1, Bao Chao1, Tegshi Muschin1
1College of Chemistry and Environmental Science, Inner Mongolia Key Laboratory of Green Catalysis, Inner Mongolia Normal University, Hohhot, 010022, China. sbbys197812@163.com.
Abstract:
The regiodivergent catalytic dehydrogenative cross-coupling reactions at both sp2 and sp3 hybridized carbons of aromatic compounds are particularly challenging. Herein, we report the finding of transient directing group controlled regiodivergent C(sp3)-C(sp2) and C(sp2)-C(sp2) cross-coupling in the o-methyl benzaldehyde frameworks. Catalyzed by palladium, using K2S2O8 or [F+] reagents as by-standing oxidants and unactivated arenes as substrates/solvents, various benzyl benzaldehydes or phenyl benzaldehydes were prepared. A mechanism study indicated that the regiospecificity is dominated by the [5,6]-fused palladacycle or [6,5]-fused palladacycle intermediates, which are generated from Pd-chelation with specified transient directing groups and further C-H activations.
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