期刊
TETRAHEDRON LETTERS
卷 57, 期 3, 页码 325-328出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.12.009
关键词
Substituent effects; Triphenylphosphine; Iodine; Anhydrides; Amides
资金
- Thailand Research Fund through the Royal Golden Jubilee Ph.D. Program [PHD/0206/2556, PHD/0086/2557]
- Center of Excellence for Innovation in Chemistry (PERCH-CIC), Chiang Mai University, Thailand
The formation of acid anhydrides from the phosphorous-mediated activation of carboxylic acids was investigated. Under various systems, activation of benzoic acid in the presence of base led to the formation of benzoic anhydride at different rates depending on the reactivity of the reagents. Using the Ph3P-I-2/Et3N combination, most aryl acids were converted into the corresponding anhydrides in high yields within 5-10 min. However, for nitro-substituted derivatives, unexpectedly, N,N-diethylamides were isolated without anhydride formation. These results indicated the pronounced effect of substituents in governing these potential side reactions which can significantly affect the yields of acylation reactions promoted by phosphonium species. (C) 2015 Elsevier Ltd. All rights reserved.
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