Regioselective formation of alpha-vinylpyrroles from the ruthenium-catalyzed coupling reaction of pyrroles and terminal alkynes involving C-H bond activation.
The cationic ruthenium catalyst Ru(3)(CO)(12)/NH(4)PF(6) was found to be highly effective for the intermolecular coupling reaction of pyrroles and terminal alkynes to give gem-selective alpha-vinylpyrroles. The carbon isotope effect on the alpha-pyrrole carbon and the Hammett correlation from a series of para-substituted N-arylpyrroles (rho = -0.90) indicate a rate-limiting C-C bond formation step of the coupling reaction.
Gao
Ruili
R
Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53201-1881, USA.
Yi
Chae S
CS
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D009942:Organometallic Compounds; D011758:Pyrroles; D012428:Ruthenium
Chem Rev. 2010 Feb 10;110(2):624-55
19438203
Angew Chem Int Ed Engl. 2009;48(35):6511-5
19630052
Acc Chem Res. 2002 Oct;35(10):826-34
12379135
Chem Rev. 2004 May;104(5):2481-506
15137797
J Am Chem Soc. 2007 Oct 10;129(40):12072-3
17880083
J Am Chem Soc. 2009 Oct 7;131(39):13888-9
19746974
Org Lett. 2009 Dec 17;11(24):5606-9
19924879
Org Lett. 2004 Oct 28;6(22):3981-3
15496079
Chem Rev. 2005 Jul;105(7):2873-920
16011327
J Am Chem Soc. 2006 Jun 28;128(25):8146-7
16787073
J Am Chem Soc. 2008 Sep 3;130(35):11604-5
18681436
J Am Chem Soc. 2005 Dec 7;127(48):17000-6
16316246
J Am Chem Soc. 2003 Apr 23;125(16):4720-1
12696885
Org Lett. 2008 Mar 20;10(6):1159-62
18278932
J Am Chem Soc. 2005 Apr 13;127(14):4996-7
15810815
J Am Chem Soc. 2006 Mar 1;128(8):2528-9
16492024
Org Lett. 2006 May 11;8(10):1979-82
16671761
Chem Commun (Camb). 2008 May 28;(20):2349-51
18473066