Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds

Ludovic Eberlin, Bertrand Carboni* and Andrew Whiting*

*UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France; Durham University, South Road, Durham DH1 3LE, U. K., Email: bertrand.carboniuniv-rennes1.fr, andy.whitingdurham.ac.uk

L. Eberlin, B. Carboni, A. Whiting, J. Org. Chem., 2015, 80, 6574-6583.

DOI: 10.1021/acs.joc.5b00593

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Abstract

In the reaction of 1,3-dienylboronic esters with nitrosoarenes, a one-pot hetero-Diels-Alder/ring contraction cascade affords N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp³ boron substituent led to the formation of stable boro-oxazines with high regioselectivity.

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Key Words

pyrroles

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ID: J42-Y2015