Ammonia Free Partial Reduction of Aromatic Compounds Using Lithium Di-tert-butylbiphenyl (LiDBB)

Timothy J. Donohoe* and David House
Dyson Perrins Laboratory, South Parks Road, Oxford OX1 3QY, U.K. timothy.donohoe@chem.ox.ac.uk
J. Org. Chem., 2002, 67 (14), pp 5015–5018
DOI: 10.1021/jo0257593
Publication Date (Web): May 29, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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The reduction of a series of hetero- and carbocyclic aromatic compounds under ammonia free conditions is described. By using LiDBB as a source of electrons, bis(methoxyethyl)amine (BMEA) as a protonating agent, and THF as a solvent, we were able to accomplish reductions more usually performed under Birch type conditions. Moreover, the use of these conditions was further enhanced by the tolerance of the reducing system toward reactive electrophiles that cannot be used successfully in ammonia.

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History

  • Published In Issue July 12, 2002
  • Received March 26, 2002

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