263408-02-2Relevant articles and documents
Ammonia free partial reduction of aromatic compounds using lithium di-tert-butylbiphenyl (LiDBB)
Donohoe, Timothy J.,House, David
, p. 5015 - 5018 (2002)
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.
Reductive aldol reactions on aromatic heterocycles
Donohoe, Timothy J.,Ace, Karl W.,Guyo, Paul M.,Helliwell, Madeleine,McKenna, Jeffrey
, p. 989 - 993 (2007/10/03)
The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn- aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd.
The partial reduction of heterocycles: An alternative to the birch reduction
Donohoe, Timothy J.,Harji, Rakesh R.,Cousins, Rick P. C.
, p. 1331 - 1334 (2007/10/03)
The partial reduction of a series of heterocycles in THF is described. By adding amine 3 as a proton source and naphthalene as an electron carrier, we were able to produce reductively alkylated pyrrolines and dihydrofurans in moderate to good yields. This reaction does not require liquid ammonia as a solvent, which may have interesting ramifications for large-scale synthesis. Moreover, we were also able to quench the reduction reactions with an acid chloride so performing a reductive acylation reaction. (C) 2000 Elsevier Science Ltd.
