Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy?
Chemical Communications Pub Date: 2021-09-29 DOI: 10.1039/D1CC04121E
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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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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