Domino C–C/C–O bond formation: palladium-catalyzed regioselective synthesis of 7-iodobenzo[b]furans using 1,2,3-triiodobenzenes and benzylketones |
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| Authors: | Raed M. Al-Zoubi Walid K. Al-Jammal Michael J. Ferguson Graham K. Murphy |
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| Affiliation: | Department of Chemistry, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110 Jordan, Fax: +962-2-7201071, +962-2-7201000 ext. 23651 ; Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton Alberta T6G2G2 Canada ; Department of Chemistry, University of Waterloo, Waterloo Ontario N2L3G1 Canada, |
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| Abstract: | A facile and efficient synthesis of 7-iodobenzo[b]furan derivatives via a highly regioselective tandem α-arylation/intramolecular O-arylation of 5-substituted-1,2,3-triiodobenzenes and benzylketones is described. Remarkably, the α-arylation coupling reactions initiate exclusively at the least sterically-hindered position of the triiodoarene, which results in a highly chemoselective transformation. The highest yields were observed in reactions between electron-poor 1,2,3-triiodoarenes and electron-rich benzylketones, yet the optimized reaction conditions were found to be tolerant to a wide range of different functional groups. This unprecedent synthesis of 7-iodobenzo[b]furans from 1,2,3-triiodobenzenes is scalable, general in scope, and provides easy access to valuable precursors for other chemical transformations.A facile and unprecedented synthesis of 7-iodobenzo[b]furans via a highly regioselective tandem α-arylation/intramolecular O-arylation is reported that is efficient, scalable and creates versatile precursors for further chemical manipulation. |
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