Facile double-lithiation of a transient urea: vicarious ortho-metalation of aniline derivatives.
A convenient one-pot method for the conversion of phenylisocyanate into ortho-functionalized aniline derivatives has been developed. The reaction proceeds via the selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithio-phenylisocyanate, a highly improbable intermediate.
Houlden
Chris E
CE
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
Lloyd-Jones
Guy C
GC
Booker-Milburn
Kevin I
KI
D000814:Aniline Compounds / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives / Q000737:chemistry*
D000814:Aniline Compounds; D009942:Organometallic Compounds; D014508:Urea; D008094:Lithium; C023650:aniline