Corrigendum to Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.
This report describes the scope and mechanism of the solvent-dependent, chemoselective oxidative coupling of 1-aryl-1,3-dicarbonyls with styrene using Ce(IV) reagents. Dihydrofuran derivatives are obtained when reactions are performed in methanol whereas nitrate esters can be selectively synthesized in acetonitrile and methylene chloride. Mechanistic studies are consistent with the rate of solvent-assisted deprotonation of a radical cation intermediate playing an integral role in the selective formation of products.
Casey
Brian M
BM
Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA.
Eakin
Cynthia A
CA
Jiao
Jingliang
J
Sadasivam
Dhandapani V
DV
Flowers
Robert A
RA
Org Lett. 2007 Mar 29;9(7):1323-6
17335227
J Nat Prod. 2004 Nov;67(11):1796-9
15568764
J Nat Prod. 1997 Apr;60(4):378-81
9182126
J Org Chem. 2007 Jul 20;72(15):5486-92
17602587
J Org Chem. 2004 Sep 17;69(19):6267-72
15357585
J Org Chem. 2006 Jul 7;71(14):5260-7
16808514
Acc Chem Res. 2004 Jan;37(1):21-30
14730991
Org Lett. 2003 Jun 26;5(13):2363-5
12816449
J Org Chem. 2005 May 13;70(10):3791-800
15876062
J Am Chem Soc. 2008 Dec 10;130(49):16494-5
19049447
J Org Chem. 2004 Jul 23;69(15):4931-5
15255718
Chem Rev. 2007 May;107(5):1862-91
17432919