Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides.
[reaction: see text] New methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides have been developed, featuring sterically demanding, electron-rich phosphines. Highly challenging electron-rich aryl chlorides, in addition to electron-neutral and electron-deficient substrates, as well as nitrogen- and sulfur-containing heteroaryl chlorides can all undergo efficient cyanation under relatively mild conditions using readily available materials. In terms of substrate scope and temperature, these methods compare very favorably with the state-of-the-art cyanations of aryl chlorides.
Littke
Adam
A
Process Research and Development, Bristol-Myers Squibb Pharmaceutical Research Institute, 1 Squibb Drive, P.O. Box 191, New Brunswick, New Jersey 08903-0191, USA. adam.littke@bms.com
Soumeillant
Maxime
M
Kaltenbach
Robert F
RF
Cherney
Robert J
RJ
Tarby
Christine M
CM
Kiau
Susanne
S
D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000138:chemical synthesis / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D000814:Aniline Compounds; D002712:Chlorides; D003486:Cyanides; D008024:Ligands; D010165:Palladium; C004658:4-chloroaniline