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A cascade double 1,4-addition/intramolecular annulation strategy for expeditious assembly of unsymmetrical dibenzofurans

, Ruxue Li, Pui Ying Choy, Mengqing Xie, Jiahui Duan, Qiang Tang, ,
Communications Chemistry , Volume 4, pp 1-10; doi:10.1038/s42004-021-00478-2

Abstract: Existing synthetic routes for accessing dibenzofuran core have intrinsic regioselectivity, limiting the substitution patterns available in heteropolycyclic arene products. Here we report a double 1,4-conjugate addition/intramolecular annulation cascade reaction between propargylamines and two equivalents of imidazolium methylides that allows efficient access of structurally versatile dibenzofurans. This transition metal-free protocol proceeds smoothly under bench-top air atmosphere and offers easy manipulation of substituents on the dibenzofuran core, and also provides good-to-excellent product yields with good functional group tolerance, particularly the –Br and –Cl groups which are often incompatible with existing metal-catalyzed C–C and/or C–O bond ring-forming processes. It is worth noting that ladder-type π-systems with all-arene quarternary carbon structure can be straightforwardly generated upon simple late-stage functionalization.
Keywords: arene / tolerance / functionalization / dibenzofuran / annulation / cascade / double / good / structurally / addition/intramolecular

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