Palladium-Catalyzed Regiodivergent Substitution of Propargylic Carbonates

被引：45
作者：
Locascio, Theresa M. [1 ]
Tunge, Jon A. [1 ]
机构：
[1] Univ Kansas, Dept Chem, 2010 Malott Hall,1251 Wescoe Hall Dr, Lawrence, KS 66045 USA
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 50期
基金：
美国国家科学基金会;
关键词：
coupling; dienylation; palladium; propargylation; CROSS-COUPLING REACTIONS; STEREOSELECTIVE-SYNTHESIS; SELECTIVE SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION; CYCLIZATION REACTIONS; ASYMMETRIC-SYNTHESIS; CASCADE REACTIONS; ALLYL; DERIVATIVES; COMPLEXES;
D O I：
10.1002/chem.201603481
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The palladium(0)-catalyzed, ligand-controlled, regioselective addition of diaryl acetonitrile pronucleophiles to propargylic carbonates is reported. Selective formation of either terminal 1,3-dienyl or propargylated products is proposed to arise from a change in reaction mechanism controlled by the denticity of the coordinating ligand.
引用
收藏
页码：18140 / 18146
页数：7
相关论文
共 124 条
[1]   2-Alkylindoles via palladium-catalyzed reductive cyclization of ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonates [J].
Ambrogio, Ilaria ;
Cacchi, Sandro ;
Fabrizi, Giancarlo .
TETRAHEDRON LETTERS, 2007, 48 (43) :7721-7725
[2]   Palladium-Catalyzed Nucleophilic Substitution of Propargylic Carbonates and Meldrum's Acid Derivatives [J].
Ambrogio, Ilaria ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Goggiamani, Antonella ;
Iazzetti, Antonia .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (14) :3147-3151
[3]   3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles [J].
Ambrogio, Ilaria ;
Cacchi, Sandro ;
Fabrizi, Giancarlo ;
Prastaro, Alessandro .
TETRAHEDRON, 2009, 65 (44) :8916-8929
[4]  
[Anonymous], 2009, ANGEW CHEM-GER EDIT
[5]  
[Anonymous], ANGEW CHEM
[6]   Construction of 1,5-Enynes by Stereospecific Pd-Catalyzed Allyl- Propargyi Cross-Couplings [J].
Ardolino, Michael J. ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (21) :8770-8773
[7]   Multicomponent decarboxylative allylations [J].
Ariyarathna, Yamuna ;
Tunge, Jon A. .
CHEMICAL COMMUNICATIONS, 2014, 50 (90) :14049-14052
[8]   Palladium-Catalyzed Allylic Alkylation of Allyl Dienol Carbonates: Reactivity, Regioselectivity, Enantioselectivity, and Synthetic Applications [J].
Arseniyadis, Stellios ;
Fournier, Jeremy ;
Thangavelu, Saravanan ;
Lozano, Oscar ;
Prevost, Sebastien ;
Archambeau, Alexis ;
Menozzi, Candice ;
Cossy, Janine .
SYNLETT, 2013, 24 (18) :2350-2364
[9]   Chemo- and enantioselective catalytic addition of propargyl chloride to aldehydes promoted by [Cr(Salen)] complexes [J].
Bandini, M ;
Cozzi, PG ;
Melchiorre, P ;
Tino, R ;
Umani-Ronchi, A .
TETRAHEDRON-ASYMMETRY, 2001, 12 (07) :1063-1069
[10]   Highly regio- and stereoselective synthesis of indene and benzo[b]furan derivatives via a Pd-catalyzed carboannulation of propargyl carbonates with nucleophiles [J].
Bi, Hai-Peng ;
Guo, Li-Na ;
Gou, Fa-Rong ;
Duan, Xin-Hua ;
Liu, Xue-Yuan ;
Liang, Yong-Min .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4713-4716
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