Pd-Catalyzed, Ligand-Enabled Stereoselective 1,2-Iodine(III) Shift/1,1-Carboxyalkynylation of Alkynylbenziodoxoles
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- 作者：Dr. Junliang Wu ; Kai Xu ; Prof. Hajime Hirao and Prof. Naohiko Yoshikai
- 刊名：Chemistry - A European Journal
- 出版年：2017
- 出版时间：January 31, 2017
- 年：2017
- 卷：23
- 期：7
- 页码：1521-1525
- 全文大小：894K
- ISSN：1521-3765
文摘
A PdII-catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk-1-en-3-ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd-assisted 1,2-iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups (the latter originating from another molecule of the alkynylbenziodoxole) into the 1-position of the transient Pd-vinylidene species. The product of this 1,1-carboxyalkynylation reaction serves as a new functionalized enyne-type building block for further synthetic transformations.