α-Acylation of Olefins via Photocatalysis

doi:10.6023/cjoc202211048

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1012-1022.DOI: 10.6023/cjoc202211048 Previous Articles Next Articles

Special Issue: 中国女科学家专辑

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光催化烯烃α-酰化反应

侯虹宇^a^,^b, 程元元^a^,^b, 陈彬^a^,^b, 佟振合^a^,^b, 吴骊珠^a^,^b^,^*()

a 中国科学院理化技术研究所光化学转换与功能材料重点实验室北京 100190
b 中国科学院大学未来技术学院北京 100049

收稿日期:2022-11-30 修回日期:2023-01-13 发布日期:2023-01-18
通讯作者: 吴骊珠
基金资助:
国家重点研发计划(2021YFA1500100); 国家重点研发计划(2022YFA1503200); 国家重点研发计划(2021YFA1500800); 国家自然科学基金(22193013); 国家自然科学基金(22088102); 国家自然科学基金(21933007); 中国科学院战略性先导科技专项(XDB17000000); 中国科学院前沿科学重点研究计划(QYZDY-SSWJSC029)

α-Acylation of Olefins via Photocatalysis

Hongyu Hou^a^,^b, Yuanyuan Cheng^a^,^b, Bin Chen^a^,^b, Chenho Tung^a^,^b, Lizhu Wu^a^,^b()

a Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190
b School of Future Technology, University of Chinese Academy of Sciences, Beijing 100049

Received:2022-11-30 Revised:2023-01-13 Published:2023-01-18
Contact: Lizhu Wu
Supported by:
National Key Research and Development Program of China(2021YFA1500100); National Key Research and Development Program of China(2022YFA1503200); National Key Research and Development Program of China(2021YFA1500800); National Natural Science Foundation of China(22193013); National Natural Science Foundation of China(22088102); National Natural Science Foundation of China(21933007); Strategic Priority Research Program of the Chinese Academy of Science(XDB17000000); Key Research Program of Frontier Sciences of the Chinese Academy of Science(QYZDY-SSWJSC029)

The cheap and readily available olefin substrates have received much attention for the synthesis of structurally rich and high value-added ketones, aldehydes, carboxylic acids and their derivatives via α-acylation. Multicomponent tandem α-acylation of olefins achieves high efficiency and selectivity by N-heterocyclic carbene or transition metal catalysis, albeit with narrow reaction modes and substrates. Rapid growth of photocatalysis in organic transformation has introduced new methodologies to undergo the α-acylation of olefins with broad substrate scope. The research progress and prospect for the future development in this active research field is highlighted.

Key words: α-acylation of olefins, difunctionalization, photocatalysis, radical cascade

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Hongyu Hou, Yuanyuan Cheng, Bin Chen, Chenho Tung, Lizhu Wu. α-Acylation of Olefins via Photocatalysis[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1012-1022.

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Fig. & Tab. 11

Scheme 1. Various catalytic strategies for α-acylation of olefins “Nu” represents “nucleophile”. “LG” represents “leaving group”. “w/o” represents “with or without”. “PC” represents “photocatalyst”. “TM” represents “transition metal”. “SET” represents “single electron transfer”

Scheme 2. Acyltrifluoromethylation of olefins by cooperative photoredox/NHC catalysis

Scheme 3. C(sp2)—H activated α-acylation of alkenes via NHC, sulfinate, and photoredox cooperative triple catalysis

Scheme 4. Alkylacylation of olefins by light-driven NHC catalysis (in parentheses is the NMR yield).

Scheme 5. Visible light-mediated NHC catalyzed unsymmetric diacylation of olefins

Scheme 6. NHC-photocatalyzed unsymmetric diacylation of olefins

Scheme 7. Visible-light-driven Ni-catalyzed diacylation of olefins

Scheme 8. Photoredox/Ni synergistically catalyzed unsymmetric diacylation of electron-deficient olefins

Scheme 9. Photoinduced Cu-catalyzed perfluoroalkylacylation of unactivated olefins

Scheme 10. Photocatalytic diacylation of olefins

Scheme 11. Photocatalyzed divergent α-acylated difunctionalization of olefins

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光催化烯烃α-酰化反应

α-Acylation of Olefins via Photocatalysis

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