Room-temperature palladium-catalyzed C-H activation: ortho-carbonylation of aniline derivatives.
Pd and CO--ureally got me! The title reaction proceeds efficiently at 18 degrees C under CO (1 atm) with 5 % [Pd(OTs)(2)(MeCN)(2)] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields (see picture, BQ = benzoquinone, Ts = 4-toluenesulfonyl).
Houlden
Chris E
CE
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Hutchby
Marc
M
Bailey
Chris D
CD
Ford
J Gair
JG
Tyler
Simon N G
SN
Gagné
Michel R
MR
Lloyd-Jones
Guy C
GC
Booker-Milburn
Kevin I
KI
D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D007096:Imidoesters / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013696:Temperature; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis / Q000737:chemistry
D000814:Aniline Compounds; D007096:Imidoesters; D062367:ortho-Aminobenzoates; D010165:Palladium; D002248:Carbon Monoxide; C038892:methyl anthranilate; C023650:aniline