Pyrrolo[2,1-a]isoquinolines as multitasking organophotocatalysts in chemical synthesis

Yuliang Liu; Haoyu Li; Eugene Yew Kun Tan; Erik Budi Santiko; Youhei Chitose; Manabu Abe; Shunsuke Chiba

doi:10.1016/j.checat.2022.08.013

Pyrrolo[2,1-a]isoquinolines as multitasking organophotocatalysts in chemical synthesis

Yuliang Liu, Haoyu Li, Eugene Yew Kun Tan, Erik Budi Santiko, Youhei Chitose, Manabu Abe^*, Shunsuke Chiba^*

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

We demonstrate the design and synthesis of pyrrolo[2,1-a]isoquinolines (PIqs) bearing electron-withdrawing groups, which are excited under irradiation with visible light to display wider redox windows and higher triplet-state energies. The photophysical and electrochemical characters of PIqs can be tailored by modification of the electron-withdrawing groups and their positions, enabling redox-neutral (hetero)biaryl cross-coupling between aryl halides and (hetero)arenes, nickel-catalyzed amination and oxygenation of aryl halides, and decarboxylative cross-coupling between α-amino acids and aryl halides, as well as a set of molecular transformations driven by triplet-triplet sensitization under irradiation with visible light.

Original language	English
Pages (from-to)	2726-2749
Number of pages	24
Journal	Chem Catalysis
Volume	2
Issue number	10
DOIs	https://doi.org/10.1016/j.checat.2022.08.013
Publication status	Published - Oct 20 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022 The Authors

ASJC Scopus Subject Areas

Chemistry (miscellaneous)
Physical and Theoretical Chemistry
Organic Chemistry

Keywords

energy transfer
photocatalysis
pyrrolo[2,1-a]isoquinolines
SDG3: Good health and well-being
SDG7: Affordable and clean energy
single-electron transfer

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10.1016/j.checat.2022.08.013

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title = "Pyrrolo[2,1-a]isoquinolines as multitasking organophotocatalysts in chemical synthesis",

abstract = "We demonstrate the design and synthesis of pyrrolo[2,1-a]isoquinolines (PIqs) bearing electron-withdrawing groups, which are excited under irradiation with visible light to display wider redox windows and higher triplet-state energies. The photophysical and electrochemical characters of PIqs can be tailored by modification of the electron-withdrawing groups and their positions, enabling redox-neutral (hetero)biaryl cross-coupling between aryl halides and (hetero)arenes, nickel-catalyzed amination and oxygenation of aryl halides, and decarboxylative cross-coupling between α-amino acids and aryl halides, as well as a set of molecular transformations driven by triplet-triplet sensitization under irradiation with visible light.",

keywords = "energy transfer, photocatalysis, pyrrolo[2,1-a]isoquinolines, SDG3: Good health and well-being, SDG7: Affordable and clean energy, single-electron transfer",

author = "Yuliang Liu and Haoyu Li and Tan, {Eugene Yew Kun} and Santiko, {Erik Budi} and Youhei Chitose and Manabu Abe and Shunsuke Chiba",

note = "Publisher Copyright: {\textcopyright} 2022 The Authors",

year = "2022",

month = oct,

day = "20",

doi = "10.1016/j.checat.2022.08.013",

language = "English",

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T1 - Pyrrolo[2,1-a]isoquinolines as multitasking organophotocatalysts in chemical synthesis

AU - Liu, Yuliang

AU - Li, Haoyu

AU - Tan, Eugene Yew Kun

AU - Santiko, Erik Budi

AU - Chitose, Youhei

AU - Abe, Manabu

AU - Chiba, Shunsuke

PY - 2022/10/20

Y1 - 2022/10/20

N2 - We demonstrate the design and synthesis of pyrrolo[2,1-a]isoquinolines (PIqs) bearing electron-withdrawing groups, which are excited under irradiation with visible light to display wider redox windows and higher triplet-state energies. The photophysical and electrochemical characters of PIqs can be tailored by modification of the electron-withdrawing groups and their positions, enabling redox-neutral (hetero)biaryl cross-coupling between aryl halides and (hetero)arenes, nickel-catalyzed amination and oxygenation of aryl halides, and decarboxylative cross-coupling between α-amino acids and aryl halides, as well as a set of molecular transformations driven by triplet-triplet sensitization under irradiation with visible light.

AB - We demonstrate the design and synthesis of pyrrolo[2,1-a]isoquinolines (PIqs) bearing electron-withdrawing groups, which are excited under irradiation with visible light to display wider redox windows and higher triplet-state energies. The photophysical and electrochemical characters of PIqs can be tailored by modification of the electron-withdrawing groups and their positions, enabling redox-neutral (hetero)biaryl cross-coupling between aryl halides and (hetero)arenes, nickel-catalyzed amination and oxygenation of aryl halides, and decarboxylative cross-coupling between α-amino acids and aryl halides, as well as a set of molecular transformations driven by triplet-triplet sensitization under irradiation with visible light.

KW - energy transfer

KW - photocatalysis

KW - pyrrolo[2,1-a]isoquinolines

KW - SDG3: Good health and well-being

KW - SDG7: Affordable and clean energy

KW - single-electron transfer

UR - http://www.scopus.com/inward/record.url?scp=85140292151&partnerID=8YFLogxK

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U2 - 10.1016/j.checat.2022.08.013

DO - 10.1016/j.checat.2022.08.013

M3 - Article

AN - SCOPUS:85140292151

SN - 2667-1107

VL - 2

SP - 2726

EP - 2749

JO - Chem Catalysis

JF - Chem Catalysis

IS - 10

ER -

Pyrrolo[2,1-a]isoquinolines as multitasking organophotocatalysts in chemical synthesis

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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