Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2049-2058.DOI: 10.6023/cjoc201505006 Previous Articles     Next Articles



张小祥a, 孙小萍a, 谈继淮a, 樊辉b, 饶卫东a   

  1. 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 常州大学石油化工学院 常州 213164
  • 收稿日期:2015-05-05 修回日期:2015-06-05 发布日期:2015-06-19
  • 通讯作者: 张小祥, 饶卫东;
  • 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(No. BK20130962)、江苏高校优势学科建设工程(PAPD)资助项目.

Progress of Nucleophilic Substitution of Allylic Alcohols

Zhang Xiaoxianga, Sun Xiaopinga, Tan Jihuaia, Fan Huib, Rao Weidonga   

  1. a Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b School of Petrochemical Engineering, Changzhou University, Changzhou 213164
  • Received:2015-05-05 Revised:2015-06-05 Published:2015-06-19
  • Supported by:

    Project supported by the Young National Natural Science Foundation of China Grant (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (No. BK20130962) and the Project Fund from the Priority Academic Program Development of Jiangsu Higher, Education Institutions (PAPD).

Nucleophilic substitution of allylic alcohols is very important in organic synthetic chemistry, which could be used for the synthesis of bioactive pharmaceutic compounds and natural compounds. One of the most powerful and efficient methods to introduce a C-3 unit is the allylic reaction. The advantage of this synthetic approach is the retention of the C=C bond in the product that can act as a handle for further functional group transformations. One synthetic strategy that has been often relied upon to introduce this functional group is the Tsuji-Trost reaction. However, a drawback of this method is the generation of waste products resulting from displacement of the leaving group on treating with a catalyst and/or nucleophile. Therefore, the direct allylation of allylic alcohols is considered as a green method. In this review, the latest research progress on the Lewis and Brønsted acids catalyzed intermolecular and intramolecular nucleophilic substitution for the formation of C—X (X=C, N, O, S) bond is presented, and a variety of nucleophiles, such as aromatical compounds, carbonyl compounds, amines or sulfonamides, alcohols and so on, are discussed. Finally, the problems and difficulties in research and application of allylation are discussed and then prospective is provided.

Key words: allylic alcohols, nucleophilic substitution, homogeneus catalyzed, allylation