Abstract
A catalytic cascade has been developed for the synthesis of biaryl-2-methyl acetates via a palladium-catalyzed ortho-C(sp2)−H bond arylation of pyruvate O-arylmethyl ketoximes with aryl iodides followed by a solvolysis, in which the pyruvic ketoxime ester as a new auxiliary is employed to direct the C(sp2)−H bond activation. The straightforward treatment of O-arylmethyl hydroxylamines and ethyl pyruvate with aryl iodides also provides the target products in a one-pot fashion. Furthermore, the new palladacycle intermediate is unambiguously confirmed by single-crystal X-ray diffraction analysis. A plausible reaction pathway is proposed for the Pd-catalyzed arylation-acetolysis sequence. (Figure presented.).
Original language | English (US) |
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Pages (from-to) | 2925-2937 |
Number of pages | 13 |
Journal | Advanced Synthesis and Catalysis |
Volume | 360 |
Issue number | 15 |
DOIs | |
State | Published - Aug 6 2018 |
Externally published | Yes |
Keywords
- C(sp)−H bond activation
- arylation
- biaryl-2-methyl acetates
- pyruvate ketoximes
- solvolysis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry