Progress of the Research on the Lewis/Brønsted Acid-Catalyzed Nucleophilic Substitution of Propargyl Alcohols

doi:10.6023/cjoc201512003

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (6): 1287-1298.DOI: 10.6023/cjoc201512003 Previous Articles Next Articles

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Lewis/Brønsted酸催化炔丙醇在亲核取代反应中的研究进展

张小祥^a, 吕昌^a, 李萍^a, 付博^a, 姚薇薇^b

a 南京林业大学化工学院江苏省生物质绿色燃料与化学品重点实验室南京 210037;
b 南京中医药大学药学院南京 210023

收稿日期:2015-12-02 修回日期:2015-12-30 发布日期:2016-02-01
通讯作者: 张小祥, 姚薇薇 E-mail:s070038@hotmail.com;yww0715@hotmail.com
基金资助:
国家自然科学青年基金(No.21302096)、江苏省自然科学青年基金(Nos.BK20130962,BK20130952)及江苏高校优势学科建设工程(PAPD)资助项目.

Progress of the Research on the Lewis/Brønsted Acid-Catalyzed Nucleophilic Substitution of Propargyl Alcohols

Zhang Xiaoxiang^a, Lü Chang^a, Li Ping^a, Fu Bo^a, Yao Weiwei^b

aJiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
b College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023

Received:2015-12-02 Revised:2015-12-30 Published:2016-02-01
Supported by:
Project supported by the Young National Natural Science Foundation of China (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (Nos. BK20130962, BK20130952) and the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Lewis/Brønsted acid-catalyzed nucleophilic substitution of propargylic alcohols is very important in organic synthetic chemistry, which could be transformed into a variety of acyclic, carbocyclic and heterocyclic synthetic building blocks. A drawback of the traditional propargylation of Nicholas reaction is the generation of waste products resulting from displacement of the leaving group on treating with a catalyst and/or nucleophile. Therefore, the direct acid-catalyzed propargylation of propargylic alcohols is considered as a green method, which generated water as the only side product. In this review, the latest research progress on the Lewis and Brønsted acids catalyzed intermolecular and intramolecular propargylation of a variety of nucleophiles (NuH=C, N, O, S, I) with propargylic alcohols is presented. Finally, the problems and difficulties in research and application of propargylation of propargylic alcohols are discussed and then prospective is provided.

Key words: propargylic alcohols, nucleophilic substitution, Lewis/Brønsted acid-catalyzed

Cite this article

Zhang Xiaoxiang, Lü Chang, Li Ping, Fu Bo, Yao Weiwei. Progress of the Research on the Lewis/Brønsted Acid-Catalyzed Nucleophilic Substitution of Propargyl Alcohols[J]. Chin. J. Org. Chem., 2016, 36(6): 1287-1298.

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Lewis/Brønsted酸催化炔丙醇在亲核取代反应中的研究进展

Progress of the Research on the Lewis/Brønsted Acid-Catalyzed Nucleophilic Substitution of Propargyl Alcohols

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