SmI2-promoted cross coupling reaction of N-2-bromoethylphthalimide and carbonyl compounds: Synthesis of α-aryl-α′-hydroxy ketones

被引:3
作者
Gonzalez-Rodriguez, Jorge [1 ]
Soto, Martin [1 ]
Soengas, Raquel G. [1 ]
Rodriguez-Solla, Humberto [1 ]
机构
[1] Univ Oviedo, Dept Organ & Inorgan Chem, Julian Claveria 8, E-33006 Oviedo, Spain
关键词
Cross coupling reaction; Samarium diiodide; alpha-Hydroxy ketones; Pinacol coupling; SAMARIUM DIIODIDE; ACYLOIN CONDENSATIONS; ORGANIC HALIDES; ALDEHYDES; CATALYST; OXYAMINATION; CYCLIZATION; CHEMISTRY; SMI2; INHIBITORS;
D O I
10.1016/j.tet.2019.130839
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper, we have disclosed the SmI2-mediated carbonyl-imide reductive cross coupling between N-2-bromoethylphthalimide and different aldehydes and ketones in the presence of anhydrous catalytic Nil(2). This methodology provided an effective tool to prepare alpha-aryl-alpha'-hydroxy ketones under mild conditions which can be applied to various functionalized, aliphatic and aromatic aldehydes and ketones. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:5
相关论文
共 76 条
[1]   Synthesis of caryose, the carbocyclic monosaccharide component of the lipopolysaccharide from Pseudomonas caryophylli [J].
Adinolfi, M ;
Barone, G ;
Iadonisi, A ;
Mangoni, L ;
Manna, R .
TETRAHEDRON, 1997, 53 (34) :11767-11780
[2]   Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation [J].
Andrus, Merritt B. ;
Hicken, Erik J. ;
Stephens, Jeffrey C. ;
Bedke, D. Karl .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8651-8654
[3]  
Annunziata R, 1999, EUR J ORG CHEM, V1999, P3369
[4]   Samarium diiodide-catalyzed diastereoselective pinacol couplings [J].
Aspinall, HC ;
Greeves, N ;
Valla, C .
ORGANIC LETTERS, 2005, 7 (10) :1919-1922
[5]   HETEROGENEOUS PERMANGANATE OXIDATIONS - AN IMPROVED PROCEDURE FOR THE DIRECT CONVERSION OF OLEFINS TO ALPHA-DIKETONES ALPHA-HYDROXY KETONES [J].
BASKARAN, S ;
DAS, J ;
CHANDRASEKARAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (21) :5182-5184
[6]   WITTIG REACTION INVOLVING A NOVEL REARRANGEMENT - CONFIRMATION BY X-RAY CRYSTALLOGRAPHY [J].
BRAIN, EG ;
CASSIDY, F ;
COX, PJ ;
SIM, GA ;
LAKE, AW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (09) :497-&
[7]   The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].
Brown, SP ;
Brochu, MP ;
Sinz, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809
[8]   An Efficient Method for the Synthesis of α-Hydroxyalkyl Aryl Ketones [J].
Chen, Chengqun ;
Feng, Xinghua ;
Zhang, Guozhen ;
Zhao, Qin ;
Huang, Guosheng .
SYNTHESIS-STUTTGART, 2008, (20) :3205-3208
[9]   Ketone-imide versus ketone-oxime reductive cross-coupling promoted by samarium diiodide:: New mechanistic insight gained from a failed aminocyclopentitol synthesis [J].
Chiara, JL ;
García, A ;
Cristóbal-Lumbroso, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4142-4151
[10]   Catalytic Ni(II) in Reactions of SmI2: Sm(II)- or Ni(0)-Based Chemistry? [J].
Choquette, Kimberly A. ;
Sadasivam, Dhandapani V. ;
Flowers, Robert A., II .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10655-10661