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
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
复制标题
酸酐催化氮杂维蒂希反应合成4H-苯并[d][1,3]恶嗪-4-酮和4-亚苄基-2-芳基恶唑-5(4H)-酮
DOI：
10.1021/acscatal.6b00165
复制
发表时间：
2016-06-01
期刊：
影响因子：
12.9
通讯作者：
Ding, Ming-Wu
中科院分区：
文献类型：
--
作者：
Wang, Long;Xie, Yi-Bi;Ding, Ming-Wu
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.
