This
paper describes a new amino-amide-based transient directing
group (TDG). The TDG can exhibit better performance in the Pd-catalyzed
arylation of aliphatic aldehydes and ketones. This reaction showed
good substrate compatibility and regioselectivity. The results indicated
that 3-amino-N-isopropylpropionamide was more beneficial
to the β-arylation of aliphatic aldehydes than other TDGs under
relatively mild conditions.
The direct Pd-catalyzed β-C–H
arylation of aldehydes
and ketones was developed by using 2-amino-N,N′-diisopropylsuccinamide as a novel transient directing
group (TDG). The TDG showed good versatility in functionalizing unactivated
β-C–H bonds of aldehydes and ketones. It was effective
not only for aliphatic aldehydes and ketones but also for aromatic
aldehydes and ketones. Besides, it was applicable to o-methylbenzaldehydes.
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