Abstract
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.
Original language | English |
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Pages (from-to) | 1521-1525 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 23 |
Issue number | 7 |
DOIs | |
Publication status | Published - 2017 Jan 31 |
Externally published | Yes |
Keywords
- alkynylation
- carboxylic acid
- cross-coupling
- hypervalent iodine
- palladium
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry