Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H-Benzo[d][1,3]oxazin-4-ones and 4-Benzylidene-2-aryloxazol-5(4H)-ones

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• 作者：Long Wang ; Yi-Bi Xie ; Nian-Yu Huang ; Jia-Ying Yan ; Wei-Min Hu ; Ming-Guo Liu ; Ming-Wu Ding
• 刊名：ACS Catalysis
• 出版年：2016
• 出版时间：June 3, 2016
• 年：2016
• 卷：6
• 期：6
• 页码：4010-4016
• 全文大小：474K
• 年卷期：0
• ISSN：2155-5435

文摘

Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.