Chinese Journal of Organic Chemistry >
Progress of Nucleophilic Substitution of Allylic Alcohols
Received date: 2015-05-05
Revised date: 2015-06-05
Online 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.
Zhang Xiaoxiang , Sun Xiaoping , Tan Jihuai , Fan Hui , Rao Weidong . Progress of Nucleophilic Substitution of Allylic Alcohols[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2049 -2058 . DOI: 10.6023/cjoc201505006
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