Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 16, Pages 3083-3089Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800458
Keywords
Microwave; C-H activation; N-benzoyl -amino ester; ruthenium; alkynes; isoquinolones
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Funding
- University of Leuven (KU Leuven)
- Erasmus Mundus Expert III
- China Scholarship Council
- COST (European Cooperation in Science and Technology) Action (CH-Activation in Organic Synthesis, CHAOS) [CA15106]
- RUDN University Program 5-100
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A microwave-assisted highly efficient intermolecular C-H functionalization sequence has been developed to access substituted isoquinolones using -amino acid esters as a directing group. This methodology enables a wide range of N-benzoyl -amino ester derivatives to react via a Ru-catalysed C-H bond activation sequence, to form isoquinolones with moderate to excellent yields. As an additional advantage, our strategy proved to be widely applicable and also enabled the reaction of alkenes to provide access to alkenylated benzamides. The methodology was also extended towards the synthesis of isoquinoline alkaloids derivatives viz. oxyavicine and a dipeptide. The developed protocol is simple and cheap, avoids tedious workup procedures and works efficiently under MW irradiation.
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