Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds

Benjamin Francois (1) , Ludovic Eberlin (1) , Fabienne Berrée (1) , Andrew Whiting (2) , Bertrand Carboni (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Durham University

Complimentary to classical hydroboration and boron-Wittig reactions, a new, efficient access to cyclic 1,3-dienyl boronic esters has been developed via diene or triene metathesis. Subsequently, fused pyrroles were synthesized with a broad substrate scope from the reaction of cyclic 1,3-dienyl boronic esters with arylnitroso compounds using a one-pot hetero-Diels-Alder/ring contraction sequence.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

Benjamin Francois, Ludovic Eberlin, Fabienne Berrée, Andrew Whiting, Bertrand Carboni. Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds. Journal of Organic Chemistry, 2020, 85 (8), pp.5173-5182. ⟨10.1021/acs.joc.9b03214⟩. ⟨hal-02563405⟩