β-Trifluoromethyl-α-functionalized-vinyl sulfides as a potential synthetic intermediate

被引：14

作者：

Hanamoto, Takeshi ^{[1
]}

Anno, Ryoko ^{[1
]}

Yamada, Kenji ^{[1
]}

Ryu, Kousuke ^{[1
]}

Maeda, Ryoko ^{[1
]}

Aoi, Kazuya ^{[1
]}

Furuno, Hiroshi ^{[2
]}

机构：

[1] Saga Univ, Dept Chem & Appl Chem, Saga 8408502, Japan

[2] Kyushu Univ, IMCE, Higashi Ku, Fukuoka 8128581, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 14期

关键词：

Trifluoromethyl group; Vinyl sulfide; Functionalization; CF(4)-Building block; USEFUL BUILDING BLOCK; DIELS-ALDER REACTION; DITHIONITE INITIATED ADDITION; ORGANIC-MOLECULES; FLUORIDE-ION; HETEROCYCLIC-COMPOUNDS; REAGENTS; 1-PHENYLSULFONYL-3,3,3-TRIFLUOROPROPENE; DERIVATIVES; 1,3-DIENES;

D O I：

10.1016/j.tet.2009.01.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The beta-(trifluoromethyl)vinyl sulfides on treatment with n-BuLi/TMEDA at -78 degrees C were readily lithiated at an a-position of the Sulfanyl group, and the generated (beta-trifluoromethyl-alpha-sulfanylvinyl anions were reacted with a variety of electrophiles to give the corresponding beta-trifluoromethyl-alpha-functionalized-vinyl sulfides 4aa-4aq in good to excellent yields. The reactivity of some products has been examined. The palladium-catalysed cross-coupling reaction as well as homo-coupling reaction of Oaf provided the corresponding products in good yields, respectively. The Diels-Alder reaction of cyclic dienes and 14 derived from 4ao provided the desired six-membered cyclic products with high endo-trifluoromethyl group selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2757 / 2765

页数：9

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