Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 34, Pages 5697-5705Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600968
Keywords
C-H activation; Rhodium; Homogeneous catalysis; Nucleobases; Nitrogen heterocycles; Nucleosides
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Funding
- Department of Science & Technology (DST, New Delhi)
- University Grants Commission (UGC, New Delhi)
- DST
- Council of Scientific and Industrial Research (CSIR, New Delhi)
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An efficient Rh-III-catalysed reaction of 2-anilinopyridines with sulfonylated alpha-diazo esters under mild conditions gave oxindole derivatives, while an analogous reaction of anilinopyrimidine precursors using alpha-diazo esters led to the ortho- alkylation products. The carbenoid coupling reaction was successfully extended to 6-anilinopurine/purine nucleosides, and the ortho-alkylated 6-anilinopurines could be obtained in excellent yields. Proof of the involvement of an Rh-C-bonded species comes from the characterisation of an intermediate-like rhodacycle (which is also an active catalyst) by single-crystal X-ray crystallography.
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