Efficient synthesis of 5-aryl-2-vinylfurans by palladium catalyzed cross-coupling strategies

被引：27

作者：

Balachari, D ^{[1
]}

Quinn, L ^{[1
]}

O'Doherty, GA ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 26期

基金：

美国国家科学基金会;

关键词：

stille coupling; cross-coupling; arylfurans; vinylfurans; palladium; organotin; organozinc;

D O I：

10.1016/S0040-4039(99)00817-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of substituted 5-aryl-2-furfurals from furfural by three alternative palladium cross coupling strategies are described. The resulting 5-aryl-2-furfurals were converted into their corresponding 5-aryl-2-vinylfurans in good yields by Wittig chemistry, (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4769 / 4773

页数：5

共 23 条

[1] PHOTOCHEMICAL-SYNTHESIS OF 3-ARYL-2-FURYL AND 5-ARYL-2-FURYL DERIVATIVES
ANTONIOLETTI, R
DAURIA, M
DEMICO, A
PIANCATELLI, G
SCETTRI, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07): : 1285 - 1288
[2] Bach T, 1998, SYNLETT, P1185
[3] Total synthesis and structural elucidation of the antifungal agent papulacandin D
Barrett, AGM
Pena, M
Willardsen, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) : 1082 - 1100
[4] PHENYLFURANS .4. SPASMOLYTIC "3-DIETHYLAMINO-2,2-(DIMETHYL)PROPYL ESTERS OF 5-SUBSTITUTED PHENYL-2-FURANCARBOXYLIC ACIDS
BURCH, HA
WHITE, RE
WRIGHT, GC
GOLDENBERG, MM
[J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1980, 69 (01) : 107 - 110
[5] Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
[6] HANEFELD W, 1994, LIEBIGS ANN CHEM, P59
[7] Syntheses of D- and L-mannose, gulose, and talose via diastereoselective and enantioselective dihydroxylation reactions
Harris, JM
Keranen, MD
O'Doherty, GA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 2982 - 2983
[8] HRIDINA, 1976, Patent No. 164654
[9] Chiral synthesis of (+)-aspicilin by using a furyl group as the masked gamma-oxo-alpha,beta-unsaturated carboxylic acid
Kobayashi, Y
Nakano, M
Okui, H
[J]. TETRAHEDRON LETTERS, 1997, 38 (51) : 8883 - 8886
[10] Substitution reactions of aryl Chlorides with organozinc reagents catalyzed by Ni(0)
Lipshutz, BH
Blomgren, PA
Kim, SK
[J]. TETRAHEDRON LETTERS, 1999, 40 (02) : 197 - 200

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