The synthesis of non-aromatic heterocyclic compounds with a coupling handle is attractive due to their potential as building blocks for saturated and unsaturated heterocycles. The first general synthesis of 4-bromo-2,3-dihydrofurans will be described. These bromine-containing heterocycles can be accessed <i>via </i>copper-mediated intramolecular cyclization of 1,2-dibromohomallylic alcohols, which are easily prepared in two steps from aromatic and aliphatic aldehydes and ketones. Competition studies revealed selectivity for 5-endo over 4-exo cyclic products, and MD simulations of representative substrates provided a rationale for the observed selectivity. Moreover, the synthetic utility of these 4-bromo-2,3-dihydrofurans in different cross-coupling reactions will be showcased.

First general preparation of 4-bromo-2,3-dihydrofurans <i>via </i>Cu-catalyzed Ullman-type reaction

ACS Spring 2022

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First general preparation of 4-bromo-2,3-dihydrofurans via Cu-catalyzed Ullman-type reaction