Premium
Synthesis of Trisubstituted Pyrroles from Rhodium‐Catalyzed Alkyne Head‐to‐Tail Dimerization and Subsequent Gold‐ Catalyzed Cyclization
Author(s) -
Peng Hong Mei,
Zhao Jing,
Li Xingwei
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800735
Subject(s) - chemistry , rhodium , hydroamination , catalysis , alkyne , medicinal chemistry , intramolecular force , selectivity , chloride , styrene , dimer , ferrocene , organic chemistry , electrode , electrochemistry , copolymer , polymer
Dimerization of N ‐protected propargylic amines in a rather rare head‐to‐tail mode has been achieved under mild conditions with high selectivity using rhodium catalysts. The N ‐protecting group could be a sulfonyl, carbamate, or carbonyl functionality and (cyclooctadiene)rhodium chloride dimer/1,1′‐bis(diphenylphosphino)ferrocene {[Rh(COD)Cl] 2 /dppf} as well as tris(triphenylphosphine)rhodium chloride [Rh(PPh 3 ) 3 Cl] proved to be active catalysts. In addition, these functionalized gem ‐enynes subsequently undergo selective gold(III)‐catalyzed intramolecular hydroamination to give trisubstituted pyrroles under mild conditions.