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Synfacts 2010(11): 1284-1284
DOI: 10.1055/s-0030-1258705
DOI: 10.1055/s-0030-1258705
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New YorkO-Arylhydroxylamines and Benzofurans via O-Arylation of Ethyl Acetohydroximate
Contributor(s):Paul Knochel, Tobias ThalerT. J. Maimone, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of O-Arylhydroxylamines and Substituted Benzofurans
J. Am. Chem. Soc. 2010, 132: 9990-9991
Massachusetts Institute of Technology, Cambridge, USA
Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of O-Arylhydroxylamines and Substituted Benzofurans
J. Am. Chem. Soc. 2010, 132: 9990-9991
Further Information
Publication History
Publication Date:
21 October 2010 (online)
Key words
O-arylation - O-arylhydroxyl-amines - benzofurans - palladium
Significance
The bulky ligands t-BuBrettPhos and t-BuXPhos were efficiently used in the palladium-catalyzed O-arylation of ethyl acetohydroximate. The resulting O-arylated products can be converted into the respective arylhydroxylamines or benzofurans.
Comment
The reaction is general, and thus a broad range of various aryl or heteroaryl halides (electron-rich and -poor) can be used. Furthermore, it offers a novel expedient access to substituted benzofurans.