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Rhodium(III)‐Catalysed Carbenoid C(sp 2 )–H Functionalisation of Aniline Substrates with α‐Diazo Esters: Formation of Oxindoles and Characterisation/Utility of an Intermediate‐Like Rhodacycle
Author(s) -
Allu Srinivasarao,
Ravi Manjula,
Kumara Swamy K. C.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600968
Subject(s) - chemistry , carbenoid , diazo , alkylation , aniline , rhodium , oxindole , coupling reaction , catalysis , medicinal chemistry , azo coupling , organic chemistry , stereochemistry
An efficient Rh III ‐catalysed reaction of 2‐anilinopyridines with sulfonylated α‐diazo esters under mild conditions gave oxindole derivatives, while an analogous reaction of anilinopyrimidine precursors using α‐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.