SiCl4-Zn induced reductive coupling of carbonyl compounds:: novel and efficient routes for one-pot syntheses of 1,2,3-triaryl-2-propen-1-ones and pinacolones at room temperature

被引：12

作者：

Salama, Tarek A. ^{[1
]}

Elmorsy, Saad S. ^{[1
]}

Khalil, Abdel-Galel M. ^{[1
]}

机构：

[1] Mansoura Univ, Fac Sci, Dept Chem, Mansoura 35516, Egypt

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 25期

关键词：

tetrachlorosilane; zinc; carbonyl compounds; reductive-coupling; rearrangement; pinacolones; 1,2,3-triaryl-2-propen-1-ones;

D O I：

10.1016/j.tetlet.2007.04.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented one-pot reductive trimerization of aromatic aldehydes to 1,2,3-triaryl-2-propen-1-ones as well as tandem reductive coupling-rearrangements of aryl ketones to pinacolone analogues was efficiently achieved using tetrachlorosilane-zinc at room temperature. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4395 / 4398

页数：4

共 44 条

[1] Silicon tetrachloride in organic synthesis: new applications for the vinylogous aldol reaction
Acocella, MR
De Rosa, M
Massa, A
Palombi, L
Villano, R
Scettri, A
[J]. TETRAHEDRON, 2005, 61 (16) : 4091 - 4097
[2] AN IMPROVED METHOD FOR THE GENERATION OF ORGANOZINC CARBENOIDS AND ITS APPLICATION IN DICARBONYL COUPLING REACTIONS
AFONSO, CAM
MOTHERWELL, WB
OSHEA, DM
ROBERTS, LR
[J]. TETRAHEDRON LETTERS, 1992, 33 (27) : 3899 - 3902
[3] OBSERVATIONS ON THE SELECTIVE DEOXYGENATION OF EPOXIDES TO OLEFINS WITH CHLOROTRIMETHYLSILANE AND ZINC
AFONSO, CAM
MOTHERWELL, WB
ROBERTS, LR
[J]. TETRAHEDRON LETTERS, 1992, 33 (23) : 3367 - 3370
[4] A simple method for the synthesis of substituted benzylic ketones: Homologation of aldehydes via the in situ generation of aryldiazomethanes from aromatic aldehydes
Angle, SR
Neitzel, ML
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) : 6458 - 6461
[5] OBSERVATIONS ON THE REDUCTIVE DEOXYGENATION OF ARYL AND ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH CHLOROTRIMETHYLSILANE AND ZINC
BANERJEE, AK
DECARRASCO, MCS
FRYDRYCHHOUGE, CSV
MOTHERWELL, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (24) : 1803 - 1805
[6] BENCZE W, 1957, J ORG CHEM, V22, P1352
[7] EVIDENCE FOR THE CIS-TRANS CONFIGURATIONS AND EFFECTIVE CONJUGATIONS OF ALPHA-PHENYLCHALCONES
BLACK, WB
LUTZ, RE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (23) : 5990 - 5997
[8] Catalytic, enantioselective α-additions of isocyanides:: Lewis base catalyzed Passerini-type reactions
Denmark, SE
Fan, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) : 9667 - 9676
[9] Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
Denmark, SE
Beutner, GL
Wynn, T
Eastgate, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3774 - 3789
[10] Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes
Denmark, SE
Heemstra, JR
[J]. ORGANIC LETTERS, 2003, 5 (13) : 2303 - 2306

← 1 2 3 4 5 →