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

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.

SUBMITTER: He X 

PROVIDER: S-EPMC9814151 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature