Silver-Catalyzed Synthesis of Enones/α-Iodoenones from Tertiary Propargyl Alcohols

被引:5
作者
Naveen, Naganaboina [1 ]
Ramesh, Golla [1 ]
Balamurugan, Rengarajan [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, India
关键词
Meyer-Schuster rearrangement; Tertiary propargyl alcohols; alpha; beta-unsaturated enones; alpha-iodoenones; AgSbF6; MEYER-SCHUSTER REARRANGEMENT; ALPHA; BETA-UNSATURATED ALDEHYDES; REDOX ISOMERIZATION; CASCADE SYNTHESIS; ALPHA-HALOENONES; GOLD; COMPLEX; KETONES; CYCLIZATION; METAL;
D O I
10.1002/slct.201903568
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tertiary propargyl alcohols undergo smooth Meyer-Schuster rearrangement to give enones in the presence of silver catalyst alone at room temperature. The intermediate can be trapped using NIS to make useful tetra substituted alpha-iodoenones.
引用
收藏
页码:13610 / 13614
页数:5
相关论文
共 112 条
[1]   Reactions of tertiary propargyl alcohols with sodium halides under oxidative conditions [J].
Aborways, Marwa M. ;
Moran, Wesley J. .
TETRAHEDRON LETTERS, 2014, 55 (13) :2127-2129
[2]   Domino Meyer-Schuster/Arylation Reaction of Alkynols or Alkynyl Hydroperoxides with Diazonium Salts Promoted by Visible Light under Dual Gold and Ruthenium Catalysis [J].
Alcaide, Benito ;
Almendros, Pedro ;
Busto, Eduardo ;
Luna, Amparo .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (09) :1526-1533
[3]   Chiral 1,1-diaryl compounds as important pharmacophores [J].
Ameen, Dana ;
Snape, Timothy J. .
MEDCHEMCOMM, 2013, 4 (06) :893-907
[4]  
[Anonymous], SCI SYNTHESIS
[5]   Microwave-Assisted Meyer-Schuster Rearrangement of Propargylic Alcohols Catalyzed by the Oxovanadate Complex [V(O)Cl(OEt)2] [J].
Antinolo, Antonio ;
Carrillo-Hermosilla, Fernando ;
Cadierno, Victorio ;
Garcia-Alvarez, Joaquin ;
Otero, Antonio .
CHEMCATCHEM, 2012, 4 (01) :123-128
[6]   Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives [J].
Bauer, Eike B. .
SYNTHESIS-STUTTGART, 2012, 44 (08) :1131-1151
[7]  
Bauer K., 2001, Common Fragrance and Flavor Materials, V4th
[8]   Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].
Binder, JT ;
Kirsch, SF .
ORGANIC LETTERS, 2006, 8 (10) :2151-2153
[9]   CONVERSIONS OF PHENYLALKYNYLCYCLOPENTANOLS TO ALPHA-IODOENONES [J].
BOVONSOMBAT, P ;
MCNELIS, E .
TETRAHEDRON LETTERS, 1993, 34 (51) :8205-8208
[10]   Isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds catalyzed by the sixteen-electron allyl-ruthenium(II) complex [Ru(η3-2-C3H4Me)(CO)(dppf)] [SbF6] [J].
Cadierno, V ;
García-Garrido, SE ;
Gimeno, J .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :101-110