A versatile catalyst for Heck reactions of aryl chlorides and aryl bromides under mild conditions.
In the presence of Cy2NMe, Pd/P(t-Bu)3 serves as an exceptionally mild and versatile catalyst for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at elevated temperature, also with high selectivity. In terms of scope and mildness, Pd/P(t-Bu)3/Cy2NMe represents an advance over previously reported catalysts for these Heck coupling processes.
Littke
A F
AF
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Fu
G C
GC
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000475:Alkenes; D006841:Hydrocarbons, Aromatic; D006842:Hydrocarbons, Brominated; D006843:Hydrocarbons, Chlorinated