Copper- or phosphine-catalyzed reaction of alkynes with isocyanides. Regioselective synthesis of substituted pyrroles controlled by the catalyst.
The copper-catalyzed reaction of isocyanides (CNCH2EWG1) 1 with electron-deficient alkynes (RC[triple bond]CEWG2) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.
Kamijo
Shin
S
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Kanazawa
Chikashi
C
Yamamoto
Yoshinori
Y
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D003486:Cyanides; D010720:Phosphines; D011758:Pyrroles; D003300:Copper