Three-component synthesis of N-Boc-4-iodopyrroles and sequential one-pot alkynylation.
(Hetero)aryl-, alkenyl-, and selected alkyl-substituted acid chlorides can be efficiently coupled with N-Boc-protected propargylamine to produce ynones which are converted in a one-pot fashion to 2-substituted N-Boc-4-iodopyrroles. Upon addition of a further alkyne, another Sonogashira coupling can be carried out in a one-pot fashion. This sequentially Pd/Cu-catalyzed process represents a very mild and efficient entry to 2,4-disubstituted N-Boc-pyrroles.
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, D-40225 Düsseldorf, Germany.
Eugen
E
Merkul
Christina
C
Boersch
Walter
W
Frank
Thomas J J
TJ
Müller
D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D006847:Hydrocarbons, Iodinated; D011437:Propylamines; D011758:Pyrroles; C009054:propargylamine; D010165:Palladium; D010293:Pargyline