Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole

James T. Brewster; Hadiqa Zafar; Matthew McVeigh; Christopher D. Wight; Gonzalo Anguera; Axel Steinbrück; Vincent M. Lynch; Jonathan L. Sessler

doi:10.1021/acs.joc.8b01333

Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole

James T. Brewster
, Hadiqa Zafar
, Matthew McVeigh
, Christopher D. Wight
, Gonzalo Anguera
, Axel Steinbrück
, Vincent M. Lynch
, Jonathan L. Sessler^*

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

8 Citations (Scopus)

Abstract

The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5″-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed.

Original language	English
Pages (from-to)	9568-9570
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	83
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.8b01333
Publication status	Published - 17 Aug 2018
Externally published	Yes

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10.1021/acs.joc.8b01333

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title = "Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole",

abstract = "The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5″-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed.",

author = "Brewster, \{James T.\} and Hadiqa Zafar and Matthew McVeigh and Wight, \{Christopher D.\} and Gonzalo Anguera and Axel Steinbr{\"u}ck and Lynch, \{Vincent M.\} and Sessler, \{Jonathan L.\}",

year = "2018",

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doi = "10.1021/acs.joc.8b01333",

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T1 - Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole

AU - Brewster, James T.

AU - Zafar, Hadiqa

AU - McVeigh, Matthew

AU - Wight, Christopher D.

AU - Anguera, Gonzalo

AU - Steinbrück, Axel

AU - Lynch, Vincent M.

AU - Sessler, Jonathan L.

PY - 2018/8/17

Y1 - 2018/8/17

N2 - The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5″-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed.

AB - The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5″-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed.

UR - https://www.scopus.com/pages/publications/85049233326

U2 - 10.1021/acs.joc.8b01333

DO - 10.1021/acs.joc.8b01333

M3 - Article

C2 - 29927588

AN - SCOPUS:85049233326

SN - 0022-3263

VL - 83

SP - 9568

EP - 9570

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole

Abstract

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