Vol.:(0123456789)
Topics in Current Chemistry (2019) 377:37
https://doi.org/10.1007/s41061-019-0265-0
1 3
REVIEW
Organocatalysis Combined with Photocatalysis
Yi‑Yin Liu
1
· Jing Liu
1
· Liang‑Qiu Lu
1
· Wen‑Jing Xiao
1
Received: 1 August 2019 / Accepted: 1 November 2019 / Published online: 15 November 2019
© Springer Nature Switzerland AG 2019
Abstract
Over the past decade, the combination of visible light photocatalysis and organocatalysis has made remarkable progress in modern chemical synthesis. In these dual
catalysis system, photocatalysts or photosensitizers absorb visible light to induce
their photoexcited states which can activate unreactive substrates via electron or
energy transfer mechanisms, and organocatalysts are usually employed to regulate
the chemical reactivity of the other substrates. By doing so, two reactive species
react with each in a selective—especially enantioselective—way, to provide the final
products. This article summarizes the recent development of cooperative catalysis
by the combination of organocatalysis and photocatalysis in asymmetric organic
synthesis. These reactions are classified according to the manner of activation of the
organocatalysts. Enamine/iminium catalysts are used to activate unreactive carbonyl
molecules. Nucleophilic catalysts including nitrogen heterocycle carbene catalysts
and tertiary amine catalysts are employed to reverse the reactivity of electrodeficient substrates including aldehydes and enals. Chiral Brønsted acid catalysts are
used to activate substrates by forming key H-bonding complexes between substrates
and catalysts.
Keywords Photocatalysis · Organocatalysis · Asymmetric · Visible light
This article is part of the Topical Collection “Asymmetric Organocatalysis Combined with Metal
Catalysis” edited by Bruce A. Arndtsen and Liu-Zhu Gong.
* Wen-Jing Xiao
wxiao@mail.ccnu.edu.cn
Liang-Qiu Lu
luliangqiu@mail.ccnu.edu.cn
1
CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide and Chemical Biology,
Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu
Road, Wuhan 430079, Hubei, China
Reprinted from the journal
67
Chapter 3 was originally published as Liu, Y-Y., Liu, J., Lu, L-Q. & Xiao, W-J. Topics in Current
Chemistry (2019) 377: 37. https://doi.org/10.1007/s41061-019-0265-0.
Topics in Current Chemistry (2019) 377:37
https://doi.org/10.1007/s41061-019-0265-0
1 3
REVIEW
Organocatalysis Combined with Photocatalysis
Yi‑Yin Liu
1
· Jing Liu
1
· Liang‑Qiu Lu
1
· Wen‑Jing Xiao
1
Received: 1 August 2019 / Accepted: 1 November 2019 / Published online: 15 November 2019
© Springer Nature Switzerland AG 2019
Abstract
Over the past decade, the combination of visible light photocatalysis and organocatalysis has made remarkable progress in modern chemical synthesis. In these dual
catalysis system, photocatalysts or photosensitizers absorb visible light to induce
their photoexcited states which can activate unreactive substrates via electron or
energy transfer mechanisms, and organocatalysts are usually employed to regulate
the chemical reactivity of the other substrates. By doing so, two reactive species
react with each in a selective—especially enantioselective—way, to provide the final
products. This article summarizes the recent development of cooperative catalysis
by the combination of organocatalysis and photocatalysis in asymmetric organic
synthesis. These reactions are classified according to the manner of activation of the
organocatalysts. Enamine/iminium catalysts are used to activate unreactive carbonyl
molecules. Nucleophilic catalysts including nitrogen heterocycle carbene catalysts
and tertiary amine catalysts are employed to reverse the reactivity of electrodeficient substrates including aldehydes and enals. Chiral Brønsted acid catalysts are
used to activate substrates by forming key H-bonding complexes between substrates
and catalysts.
Keywords Photocatalysis · Organocatalysis · Asymmetric · Visible light
This article is part of the Topical Collection “Asymmetric Organocatalysis Combined with Metal
Catalysis” edited by Bruce A. Arndtsen and Liu-Zhu Gong.
* Wen-Jing Xiao
wxiao@mail.ccnu.edu.cn
Liang-Qiu Lu
luliangqiu@mail.ccnu.edu.cn
1
CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide and Chemical Biology,
Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu
Road, Wuhan 430079, Hubei, China
Reprinted from the journal
67
Chapter 3 was originally published as Liu, Y-Y., Liu, J., Lu, L-Q. & Xiao, W-J. Topics in Current
Chemistry (2019) 377: 37. https://doi.org/10.1007/s41061-019-0265-0.