Suzuki-Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π···S···π interaction

Takuhei Yamamoto; Malika Ammam; Sue A. Roberts; George S. Wilson; Richard S. Glass

doi:10.1016/j.tet.2016.03.040

Suzuki-Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π···S···π interaction

Takuhei Yamamoto, Malika Ammam, Sue A. Roberts, George S. Wilson, Richard S. Glass

Chemistry and Biochemistry

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

4 Scopus citations

Abstract

S-tert-Butyl m-terphenyl thioethers have been efficiently synthesized by Suzuki-Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π···S···π interactions.

Original language	English (US)
Pages (from-to)	2527-2534
Number of pages	8
Journal	Tetrahedron
Volume	72
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2016.03.040
State	Published - May 19 2016

Keywords

Electrochemistry
Regioselectivity
Unsymmetrical substitution

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Suzuki-Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π···S···π interaction",

abstract = "S-tert-Butyl m-terphenyl thioethers have been efficiently synthesized by Suzuki-Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π···S···π interactions.",

keywords = "Electrochemistry, Regioselectivity, Unsymmetrical substitution",

author = "Takuhei Yamamoto and Malika Ammam and Roberts, {Sue A.} and Wilson, {George S.} and Glass, {Richard S.}",

note = "Funding Information: The authors gratefully acknowledge financial support of this work by the National Science Foundation (Grant No. 0956581 ). ",

year = "2016",

month = may,

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doi = "10.1016/j.tet.2016.03.040",

language = "English (US)",

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T1 - Suzuki-Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π···S···π interaction

AU - Yamamoto, Takuhei

AU - Ammam, Malika

AU - Roberts, Sue A.

AU - Wilson, George S.

AU - Glass, Richard S.

N1 - Funding Information: The authors gratefully acknowledge financial support of this work by the National Science Foundation (Grant No. 0956581 ).

PY - 2016/5/19

Y1 - 2016/5/19

N2 - S-tert-Butyl m-terphenyl thioethers have been efficiently synthesized by Suzuki-Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π···S···π interactions.

AB - S-tert-Butyl m-terphenyl thioethers have been efficiently synthesized by Suzuki-Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π···S···π interactions.

KW - Electrochemistry

KW - Regioselectivity

KW - Unsymmetrical substitution

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