Citation: Wei Xiao, Jie Wu. Recent advance in carbocation-catalyzed reactions[J]. Chinese Chemical Letters, ;2023, 34(2): 107637. doi: 10.1016/j.cclet.2022.06.060 shu

Recent advance in carbocation-catalyzed reactions

Wei Xiao ^a ,
Jie Wu ^{a, b, c, *,}

a.
School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, Taizhou 318000, China
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
c.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

jie_wu@fudan.edu.cn

Received Date: 26 April 2022
Revised Date: 14 June 2022
Accepted Date: 21 June 2022
Available Online: 26 June 2022

Figures(37)

Carbocations such as tropylium and trityl cation, can be stable enough to be isolated and used without inert conditions. They can act as Lewis acids to lower the LUMO of electrophile, thus promoting reactions with nucleophiles. Additionally, the interaction between carbocations and alcohols can form Brønsted acids with enhanced acidity. Furthermore, electrophoto activation of TAC⁺ (trisaminocyclopropenium ion) delivers the excited radical dication TAC^•2+*, which is a strong oxidant and capable of oxidizing a range of challenging substrates. Moreover, Pr-DMQA⁺ is disclosed as a versatile photoredox catalyst as its excited state can be quenched through both oxidation and reduction. This review summarizes recent advance in carbocation-catalyzed reactions. These developed methods provide an environmentally friendly pathway for the synthesis of valuable compounds and will inspire chemists to discover more interesting transformations promoted by carbocations.
- Carbocation,
- Lewis acid,
- Photoredox catalysis,
- Tropylium cation,
- Trityl cation
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