Citation:
Meihui Cai, Yi Huang, Xingxing Ma, Qiuling Song. Exploring the Mysteries of the Petasis-Boronic Acid-Mannich Reaction[J]. University Chemistry,
;2025, 40(11): 184-190.
doi:
10.12461/PKU.DXHX202412054
-
This review provides a comprehensive examination of the Petasis-boronic acid-Mannich reaction, systematically elucidating its origin, reaction mechanism, research progress, and applications in organic synthesis. As a significant advancement in organoboron chemistry, this reaction represents an innovative extension of the traditional Mannich reaction and contributes to the enrichment of university-level organic chemistry curricula. By introducing the Petasis-boronic acid-Mannich reaction, this work aims to enhance students’ understanding of advanced organic reactions while fostering their interest and enthusiasm for exploring the field of organoboron chemistry, building upon their foundational knowledge of the classical Mannich reaction.
-
-
-
[1]
-
[2]
Mannich, C. Arch. Pharm, 1917, 255, 261.
-
[3]
Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34 (4), 583.
-
[4]
Carrera, D. E. Chem. Commun. 2017, 53 (81), 11185.
-
[5]
Prakash, G. S.; Mandal, M.; Schweizer, S.; Petasis, N. A.; Olah, G. A. Org. Lett. 2000, 2 (20), 3173.
-
[6]
Lee, H.; Song, K. H.; Lee, S. J. Org. Chem. 2024, 89 (19), 14527.
-
[7]
Mundal, D. A.; Lutz, K. E.; Thomson, R. J. J. Am. Chem. Soc. 2012, 134 (13), 5782.
-
[8]
Cannillo, A.; Norsikian, S.; Tran Huu Dau, M. E.; Retailleau, P.; Iorga, B. I.; Beau, J. M. Chem-Eur. J. 2014, 20 (38), 12133.
-
[9]
Chrzanowska, M.; Grajewska, A.; Meissner, Z.; Rozwadowska, M.; Wiatrowska, I. Tetrahedron 2012, 68 (14), 3092.
-
[10]
Sridhar, T.; Berrée, F.; Sharma, G. V. M.; Carboni, B. J. Org. Chem., 2014, 79 (2), 783.
-
[11]
Bozorov, K.; Nie, L. F.; Zhao, J.; Aisa, H. A. Eur. J. Med. Chem. 2017, 140 (10), 465.
-
[12]
Hwang, J.; Borgelt, L.; Wu, P. ACS Comb. Sci. 2020, 22 (10), 495.
-
[13]
Das, B. C.; Adil Shareef, M.; Das, S.; Nandwana, N. K.; Das, Y.; Saito, M.; Weiss, L. M. Bioorg. Med. Chem. 2022, 63 (1), 116748.
-
[14]
Dustin, D.; Youmans, A. M.; Levi, M. S. Org. Lett., 2024, 26 (35), 7297.
-
[15]
Rimpiläinen, T.; Andrade, J.; Nunes, A.; Ntungwe, E.; Fernandes, A. S.; Vale, J. R.; Gomes, J. P.; Rijo, P.; Candeias, N. R. ACS Omega. 2018, 3 (11), 16191.
-
[1]
-
-
-
[1]
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
-
[2]
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
-
[3]
Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
-
[4]
Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
-
[5]
Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
-
[6]
Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
-
[7]
Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
-
[8]
Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
-
[9]
Yansong Xiao , Yi Huang , Xingxing Ma , Qiuling Song . The Matteson Reaction in Organic Synthesis: From Fundamentals to Frontiers. University Chemistry, 2025, 40(10): 114-120. doi: 10.12461/PKU.DXHX202411023
-
[10]
Ruige ZHANG , Zhe ZHANG , He ZHENG , Zhan SHI . Recent advances of metal-organic frameworks for alkaline electrocatalytic oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2011-2028. doi: 10.11862/CJIC.20250185
-
[11]
Ruoqian Zhang , Chaoqun Mu , Yali Hou , Mingming Zhang . 四苯乙烯基多组分金属有机笼的构筑及其固态发光性能研究. University Chemistry, 2025, 40(8): 277-283. doi: 10.12461/PKU.DXHX202410027
-
[12]
Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
-
[13]
Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
-
[14]
Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO2 Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
-
[15]
Yihong Shao , Rongchen Shen , Song Wang , Shijie Li , Peng Zhang , Xin Li . Composition engineering in covalent organic frameworks for tailored photocatalysis. Acta Physico-Chimica Sinica, 2025, 41(12): 100176-0. doi: 10.1016/j.actphy.2025.100176
-
[16]
Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO2 Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
-
[17]
Weicheng Feng , Jingcheng Yu , Yilan Yang , Yige Guo , Geng Zou , Xiaoju Liu , Zhou Chen , Kun Dong , Yuefeng Song , Guoxiong Wang , Xinhe Bao . Regulating the High Entropy Component of Double Perovskite for High-Temperature Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(6): 2306013-0. doi: 10.3866/PKU.WHXB202306013
-
[18]
Houjin Li , Wenjian Lan . Name Reactions in University Organic Chemistry Laboratory. University Chemistry, 2024, 39(4): 268-279. doi: 10.3866/PKU.DXHX202310016
-
[19]
Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
-
[20]
Shuixing Dai , Jilei Jiang , Yuxiao Wang , Jinqi Hu , Minghua Huang . Application of Knoevenagel Reaction in Organic Chemistry Teaching. University Chemistry, 2025, 40(5): 334-341. doi: 10.12461/PKU.DXHX202405208
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(160)
- HTML views(13)
Login In
DownLoad: