Direct and indirect electrochemical generation of alkoxycarbenium ion pools from thioacetals

Kouichi Matsumoto; Koji Ueoka; Shinkiti Suzuki; Seiji Suga; Jun ichi Yoshida

doi:10.1016/j.tet.2009.09.020

Direct and indirect electrochemical generation of alkoxycarbenium ion pools from thioacetals

Kouichi Matsumoto, Koji Ueoka, Shinkiti Suzuki, Seiji Suga, Jun ichi Yoshida

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

32 Citations (Scopus)

Abstract

Thioacetals were found to be effective precursors to generate and accumulate alkoxycarbenium ions based on direct and indirect cation pool methods. Alkoxycarbenium ions thus generated reacted with carbon nucleophiles such as allylsilanes and enol silyl ethers to give C-C bond formation products in good yields.

Original language	English
Pages (from-to)	10901-10907
Number of pages	7
Journal	Tetrahedron
Volume	65
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2009.09.020
Publication status	Published - Dec 26 2009
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.09.020

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title = "Direct and indirect electrochemical generation of alkoxycarbenium ion pools from thioacetals",

abstract = "Thioacetals were found to be effective precursors to generate and accumulate alkoxycarbenium ions based on direct and indirect cation pool methods. Alkoxycarbenium ions thus generated reacted with carbon nucleophiles such as allylsilanes and enol silyl ethers to give C-C bond formation products in good yields.",

author = "Kouichi Matsumoto and Koji Ueoka and Shinkiti Suzuki and Seiji Suga and Yoshida, {Jun ichi}",

note = "Funding Information: This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science. The authors thank Prof. Dr. Hendrik Zipse of Ludwig-Maximilians-Universit{\"a}t M{\"u}nchen for fruitful discussions. K.M acknowledges JSPS for financial support.",

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T1 - Direct and indirect electrochemical generation of alkoxycarbenium ion pools from thioacetals

AU - Matsumoto, Kouichi

AU - Ueoka, Koji

AU - Suzuki, Shinkiti

AU - Suga, Seiji

AU - Yoshida, Jun ichi

N1 - Funding Information: This work was financially supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science. The authors thank Prof. Dr. Hendrik Zipse of Ludwig-Maximilians-Universität München for fruitful discussions. K.M acknowledges JSPS for financial support.

PY - 2009/12/26

Y1 - 2009/12/26

N2 - Thioacetals were found to be effective precursors to generate and accumulate alkoxycarbenium ions based on direct and indirect cation pool methods. Alkoxycarbenium ions thus generated reacted with carbon nucleophiles such as allylsilanes and enol silyl ethers to give C-C bond formation products in good yields.

AB - Thioacetals were found to be effective precursors to generate and accumulate alkoxycarbenium ions based on direct and indirect cation pool methods. Alkoxycarbenium ions thus generated reacted with carbon nucleophiles such as allylsilanes and enol silyl ethers to give C-C bond formation products in good yields.

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U2 - 10.1016/j.tet.2009.09.020

DO - 10.1016/j.tet.2009.09.020

M3 - Article

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EP - 10907

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 52

ER -

Direct and indirect electrochemical generation of alkoxycarbenium ion pools from thioacetals

Abstract

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