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DOI: 10.1055/s-2007-991235
Synthesis of Acetophenones via Regioselective Arylation of Vinyl Ethers
Contributor(s):Paul Knochel, Andrei GavryushinUppsala University, Sweden and Università degli Studi di Siena, Italy
Highly Regioselective Internal Heck Arylation of Hydroxyalkyl Vinyl Ethers by Aryl Halides in Water
J. Org. Chem. 2007, 72: 6390-6396
Publication History
Publication Date:
23 October 2007 (online)
Key words
Heck reaction - acetophenones - aryl halides
Significance
This interesting and elegant protocol for the Heck arylation reaction in water is also a quite synthetically useful method for the mild preparation of acetophenones from aryl halides. The reaction is usually completely regioselective and affords high yields of products after the hydrolysis. Functional groups and ortho-substituents in substrates are well tolerated. This method can also be applied to some aryl chlorides and heteroarenes.
Comment
Hydroxyethyl vinyl ether is relatively inexpensive and has been used for the conversion of aryl halides or sulfonates into acetophenones. A similar arylation reaction with an aryl triflate (in MeCN) was applied by the same group for the synthesis of new HIV protease inhibitors (A. Arefalk, J. Wannberg, M. Larhed, A. Hallberg J. Org. Chem. 2006, 71, 1265). Electron-poor heterocycles (pyridines) are poor substrates, while thiophene gives very good results.