A one-pot dilithiation-lithium-zinc exchange-Negishi coupling approach to 2,6-di(hetero)aryl substituted dithienothiazines-a novel class of electronically fine-tunable redox systems

Catherine Dostert; Thomas J.J. Müller

doi:10.1039/c5qo00046g

A one-pot dilithiation-lithium-zinc exchange-Negishi coupling approach to 2,6-di(hetero)aryl substituted dithienothiazines-a novel class of electronically fine-tunable redox systems

Catherine Dostert
, Thomas J.J. Müller^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

2,6-Di(hetero)aryl and 2-(hetero)aryl substituted dithienothiazines are prepared from N-aryl dithienothiazines by a lithiation-lithium-zinc exchange-Negishi cross-coupling sequence with (hetero)aryl iodides in a one-pot fashion in good to excellent yields. These novel extended π-electron systems can be reversibly oxidized and fine-tuned in their electronic properties as supported by cyclo voltammetric, and absorption and emission spectroscopic studies.

Original language	English
Pages (from-to)	481-491
Number of pages	11
Journal	Organic Chemistry Frontiers
Volume	2
Issue number	5
DOIs	https://doi.org/10.1039/c5qo00046g
Publication status	Published - May 2015
Externally published	Yes

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title = "A one-pot dilithiation-lithium-zinc exchange-Negishi coupling approach to 2,6-di(hetero)aryl substituted dithienothiazines-a novel class of electronically fine-tunable redox systems",

abstract = "2,6-Di(hetero)aryl and 2-(hetero)aryl substituted dithienothiazines are prepared from N-aryl dithienothiazines by a lithiation-lithium-zinc exchange-Negishi cross-coupling sequence with (hetero)aryl iodides in a one-pot fashion in good to excellent yields. These novel extended π-electron systems can be reversibly oxidized and fine-tuned in their electronic properties as supported by cyclo voltammetric, and absorption and emission spectroscopic studies.",

author = "Catherine Dostert and M{\"u}ller, \{Thomas J.J.\}",

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year = "2015",

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doi = "10.1039/c5qo00046g",

language = "English",

volume = "2",

pages = "481--491",

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publisher = "Royal Society of Chemistry",

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A one-pot dilithiation-lithium-zinc exchange-Negishi coupling approach to 2,6-di(hetero)aryl substituted dithienothiazines-a novel class of electronically fine-tunable redox systems. / Dostert, Catherine; Müller, Thomas J.J.
In: Organic Chemistry Frontiers, Vol. 2, No. 5, 05.2015, p. 481-491.

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

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AU - Müller, Thomas J.J.

PY - 2015/5

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N2 - 2,6-Di(hetero)aryl and 2-(hetero)aryl substituted dithienothiazines are prepared from N-aryl dithienothiazines by a lithiation-lithium-zinc exchange-Negishi cross-coupling sequence with (hetero)aryl iodides in a one-pot fashion in good to excellent yields. These novel extended π-electron systems can be reversibly oxidized and fine-tuned in their electronic properties as supported by cyclo voltammetric, and absorption and emission spectroscopic studies.

AB - 2,6-Di(hetero)aryl and 2-(hetero)aryl substituted dithienothiazines are prepared from N-aryl dithienothiazines by a lithiation-lithium-zinc exchange-Negishi cross-coupling sequence with (hetero)aryl iodides in a one-pot fashion in good to excellent yields. These novel extended π-electron systems can be reversibly oxidized and fine-tuned in their electronic properties as supported by cyclo voltammetric, and absorption and emission spectroscopic studies.

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U2 - 10.1039/c5qo00046g

DO - 10.1039/c5qo00046g

M3 - Article

AN - SCOPUS:84946828254

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JO - Organic Chemistry Frontiers

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ER -

A one-pot dilithiation-lithium-zinc exchange-Negishi coupling approach to 2,6-di(hetero)aryl substituted dithienothiazines-a novel class of electronically fine-tunable redox systems

Abstract

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