Nucleophilic Organocatalysis through Umpolung

Adv search

Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (05): 545-564. Next Articles

Review

经过极性反转的亲核有机催化

于海珠，傅尧，刘磊，郭庆祥*

(中国科学技术大学化学系合肥 230026)

收稿日期:2006-03-06 修回日期:1900-01-01 发布日期:2007-05-10
通讯作者: 郭庆祥

Nucleophilic Organocatalysis through Umpolung

YU Hai-Zhu, FU Yao, LIU Lei, GUO Qing-Xiang*

(Department of Chemistry, University of Science and Technology of China, Hefei 230026)

Received:2006-03-06 Revised:1900-01-01 Published:2007-05-10

Contact: GUO Qing-Xiang

Share

PDF
2470

Knowledge
0

Cited
2

Abstract

In this review the recent advances in this field are summarized and the catalysts using C, N, P and S as the nucleophilic center were surveyed. The performances of different catalysts in a variety of reactions are analyzed. The possible umpolung mechanisms of these catalysts are discussed.

Key words: umpolung, heterocyclic carbene, nucleophilic organocatalysis

Cite this article

YU Hai-Zhu, FU Yao, LIU Lei, GUO Qing-Xiang*. Nucleophilic Organocatalysis through Umpolung[J]. Chin. J. Org. Chem., 2007, 27(05): 545-564.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

()

References

Related Articles 15

[1] Dengpeng Xia, Jinyun Luo, Lin He, Zhihua Cai, Guangfen Du. N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 622-630.

[2] Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.

[3] Yuanlin Cai, Ya Lü, Guihua Nie, Zhichao Jin, Yonggui Chi. Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3135-3145.

[4] Liangru Yang, Mengli Guo, Jinwei Yuan, Jiamei Wangx, Yuting Xia, Yongmei Xiao, Pu Mao. Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2002-2025.

[5] Xinyu Zhang, Huihui Geng, Shilei Zhang, Wei Wang, Xiaobei Chen. A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1510-1516.

[6] Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.

[7] Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.

[8] Guijie Liu, Zhengqiang Fu, Fei Chen, Caixia Xu, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO₂ and Epoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 629-635.

[9] Wei Zhao, Jing Liu, Xiangkui He, Hao Jiang, Liangqiu Lu, Wenjing Xiao. N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2504-2514.

[10] Ting Yao, Jiayan Li, Jiaming Wang, Changgui Zhao. Recent Advances for the Construction of Seven-Membered Ring Catalyzed by N-Heterocyclic Carbenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 925-944.

[11] Zhupeng Gao, Kai Xiang, Xuetao Xu, Yating Zhang, Daoyong Zhu. α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3766-3775.

[12] Xianghui Meng, Liangru Yang, Qilin Liu, Zhenhua Dong, Jinwei Yuan, Yongmei Xiao, Pu Mao. Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3747-3756.

[13] Rong Wang, Lichen Xu, Yi Lu, Bo Jiang, Wenjuan Hao. Sc(OTf)₃-Catalyzed Dearomatization of Indoles for the Synthesis of 3,3'-Bisindoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1582-1590.

[14] Li Cheng, Wenrong Wang, Yuqian Sun, Tuanjie Li, Chenxia Yu, Changsheng Yao. N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1607-1613.

[15] Yuxia Zhang, Jingcheng Guo, Jie Huang, Zhenqian Fu. N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4467-4475.

Recommended Articles

Metrics

Viewed

Full text

Abstract

Comments

Abstract

References

Related Articles

Recommended Articles

Metrics

Comments

TOP

About

About Chinese Journal of Organic Chemistry

Editorial board

Impact factor

Indexed in

Browse

Just accepted

Current issue

Archives

Hot papers

Special issues

Most cited

Most viewed

Most downloaded

Author center

Author guide

Submit

Downloads

Stay connected

RSS

Email alert

Subscribe

Contact

Contact us

Advertisement

ISSN: 0253-2786 CN: 31-1321/06

Address: No.345 Lingling Road, Shanghai, PRC

Postcode: 200032

Tel: 021-54925244

Fax: +086-021-54925285

E-mail: yjhx@sioc.ac.cn

© 2019Shanghai Institute of Organic Chemistry 、Chinese Chemical Society

[1]	Dengpeng Xia, Jinyun Luo, Lin He, Zhihua Cai, Guangfen Du. N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 622-630.
[2]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[3]	Yuanlin Cai, Ya Lü, Guihua Nie, Zhichao Jin, Yonggui Chi. Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3135-3145.
[4]	Liangru Yang, Mengli Guo, Jinwei Yuan, Jiamei Wangx, Yuting Xia, Yongmei Xiao, Pu Mao. Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2002-2025.
[5]	Xinyu Zhang, Huihui Geng, Shilei Zhang, Wei Wang, Xiaobei Chen. A Method for the Synthesis of Deuterated Benzoins Catalyzed by N-Heterocyclic Carbene [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1510-1516.
[6]	Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.
[7]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[8]	Guijie Liu, Zhengqiang Fu, Fei Chen, Caixia Xu, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Manganese Complex/ Tetrabutylammonium Iodide Catalyzed Synthesis of Cyclic Carbonate from CO₂ and Epoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 629-635.
[9]	Wei Zhao, Jing Liu, Xiangkui He, Hao Jiang, Liangqiu Lu, Wenjing Xiao. N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2504-2514.
[10]	Ting Yao, Jiayan Li, Jiaming Wang, Changgui Zhao. Recent Advances for the Construction of Seven-Membered Ring Catalyzed by N-Heterocyclic Carbenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 925-944.
[11]	Zhupeng Gao, Kai Xiang, Xuetao Xu, Yating Zhang, Daoyong Zhu. α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3766-3775.
[12]	Xianghui Meng, Liangru Yang, Qilin Liu, Zhenhua Dong, Jinwei Yuan, Yongmei Xiao, Pu Mao. Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3747-3756.
[13]	Rong Wang, Lichen Xu, Yi Lu, Bo Jiang, Wenjuan Hao. Sc(OTf)₃-Catalyzed Dearomatization of Indoles for the Synthesis of 3,3'-Bisindoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1582-1590.
[14]	Li Cheng, Wenrong Wang, Yuqian Sun, Tuanjie Li, Chenxia Yu, Changsheng Yao. N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1607-1613.
[15]	Yuxia Zhang, Jingcheng Guo, Jie Huang, Zhenqian Fu. N-Heterocyclic Carbene-Catalyzed [4+2] Annulation of Acetates and β-Silyl Enones: Highly Enantioselective Synthesis of β-Silyl δ-Lactones [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4467-4475.