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Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations

Conway, Benjamin Grant and Crosbie, Elaine and Kennedy, Alan and Mulvey, Robert E. and Robertson, Stuart D. (2012) Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations. Chemical Communications, 48 (39). pp. 4674-4676. ISSN 1359-7345

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Abstract

As the aluminate base [LiAl(TMP)(2)(iBu)(2)] 1 displays halogen tolerance towards substituted aromatics, 4-halo-anisoles have been ortho-aluminated and electrophilically quenched to form synthetically useful multi-heterohalogenated anisoles, with the Al intermediates along the route structurally defined.