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

Takeshi Hanamoto; Ryoko Anno; Kenji Yamada; Kousuke Ryu; Ryoko Maeda; Kazuya Aoi; Hiroshi Furuno

doi:10.1016/j.tet.2009.01.097

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

Takeshi Hanamoto, Ryoko Anno, Kenji Yamada, Kousuke Ryu, Ryoko Maeda, Kazuya Aoi, Hiroshi Furuno

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

The β-(trifluoromethyl)vinyl sulfides on treatment with n-BuLi/TMEDA at -78 °C were readily lithiated at an α-position of the sulfanyl group, and the generated β-trifluoromethyl-α-sulfanylvinyl anions were reacted with a variety of electrophiles to give the corresponding β-trifluoromethyl-α-functionalized-vinyl sulfides 4aa-4aq in good to excellent yields. The reactivity of some products has been examined. The palladium-catalyzed cross-coupling reaction as well as homo-coupling reaction of 4af 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.

Original language	English
Pages (from-to)	2757-2765
Number of pages	9
Journal	Tetrahedron
Volume	65
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2009.01.097
Publication status	Published - Apr 4 2009

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.01.097

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title = "β-Trifluoromethyl-α-functionalized-vinyl sulfides as a potential synthetic intermediate",

abstract = "The β-(trifluoromethyl)vinyl sulfides on treatment with n-BuLi/TMEDA at -78 °C were readily lithiated at an α-position of the sulfanyl group, and the generated β-trifluoromethyl-α-sulfanylvinyl anions were reacted with a variety of electrophiles to give the corresponding β-trifluoromethyl-α-functionalized-vinyl sulfides 4aa-4aq in good to excellent yields. The reactivity of some products has been examined. The palladium-catalyzed cross-coupling reaction as well as homo-coupling reaction of 4af 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.",

author = "Takeshi Hanamoto and Ryoko Anno and Kenji Yamada and Kousuke Ryu and Ryoko Maeda and Kazuya Aoi and Hiroshi Furuno",

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T1 - β-Trifluoromethyl-α-functionalized-vinyl sulfides as a potential synthetic intermediate

AU - Hanamoto, Takeshi

AU - Anno, Ryoko

AU - Yamada, Kenji

AU - Ryu, Kousuke

AU - Maeda, Ryoko

AU - Aoi, Kazuya

AU - Furuno, Hiroshi

PY - 2009/4/4

Y1 - 2009/4/4

N2 - The β-(trifluoromethyl)vinyl sulfides on treatment with n-BuLi/TMEDA at -78 °C were readily lithiated at an α-position of the sulfanyl group, and the generated β-trifluoromethyl-α-sulfanylvinyl anions were reacted with a variety of electrophiles to give the corresponding β-trifluoromethyl-α-functionalized-vinyl sulfides 4aa-4aq in good to excellent yields. The reactivity of some products has been examined. The palladium-catalyzed cross-coupling reaction as well as homo-coupling reaction of 4af 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.

AB - The β-(trifluoromethyl)vinyl sulfides on treatment with n-BuLi/TMEDA at -78 °C were readily lithiated at an α-position of the sulfanyl group, and the generated β-trifluoromethyl-α-sulfanylvinyl anions were reacted with a variety of electrophiles to give the corresponding β-trifluoromethyl-α-functionalized-vinyl sulfides 4aa-4aq in good to excellent yields. The reactivity of some products has been examined. The palladium-catalyzed cross-coupling reaction as well as homo-coupling reaction of 4af 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.

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JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

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

Abstract

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