ortho-Lithiation Reactions of O-(3,n-Dihalophenyl) N,N-Diethylcarbamates: Synthesis of Dihalosalicylamides and 2,3,n-Trihalophenol Derivatives

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ortho-Lithiation Reactions of O-(3,n-Dihalophenyl) N,N-Diethylcarbamates: Synthesis of Dihalosalicylamides and 2,3,n-Trihalophenol Derivatives Feberero, Claudia Velasco, Rocío Sanz Díez, Roberto New dihalosalicylamides and trihalophenol derivatives have been synthesized from easily available O-(3,n-dihalophenyl) N,N-diethylcarbamates by using a directed ortho-metalation (DoM) strategy. The o-lithiation reactions with sBuLi take place regioselectively at the doubly activated C-2 position, which demonstrates the ability of O-carbamates as directed metalating groups. In addition, highly functionalized arylnitriles were accessed from organolithium intermediates by using a tandem transnitrilation/SNAr reaction sequence. 2016-11-24 2017-11-01 2016-11 info:eu-repo/semantics/article 1434-193X http://hdl.handle.net/10259/4281 spa European Journal of Organic Chemistry. 2016, n. 33, p. 5445–5587 http://dx.doi.org/10.1002/ejoc.201600933 info:eu-repo/semantics/openAccess Wiley-VCH Verlag