Facile synthesis of N-aryl pyrroles via Cu(II)-mediated cross coupling of electron deficient pyrroles and arylboronic acids.
N-Arylation of electron-deficient pyrroles has been achieved by cross-coupling with arylboronic acids at room temperature in the presence of stoichiometric amounts of copper(II) acetate. The generality of this reaction has been established with variously substituted pyrroles as well as boronic acids. A key intermediate in the synthesis of a matrix metalloprotease inhibitor has been achieved using this methodology.
Yu
Shu
S
Chemical Research and Development, Pfizer Global Research & Development-La Jolla, 3565 General Atomics Court, San Diego, California 92121, USA.
Saenz
James
J
Srirangam
Jayaram K
JK
D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D003300:Copper / Q000737:chemistry*; D004353:Drug Evaluation, Preclinical; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006038:Glyoxylates / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004364:Pharmaceutical Preparations / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
C452459:AG3433; D001713:Biphenyl Compounds; D001897:Boronic Acids; D004791:Enzyme Inhibitors; D005663:Furans; D006038:Glyoxylates; D009570:Nitriles; D004364:Pharmaceutical Preparations; D011758:Pyrroles; C452479:ethyl N-(4'-cyanobiphenyl-4-yl)-5-formylpyrrole-3-glyoxalate; D003300:Copper