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The partial reduction of heterocycles: an alternative to the Birch reduction

Abstract:
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.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON LETTERS
Volume:
41
Issue:
9
Pages:
1331-1334
Publication date:
2000-02-26
DOI:
ISSN:
0040-4039
URN:
uuid:ba01572a-cf5f-454a-ae38-4d1a6055ba10
Source identifiers:
37328
Local pid:
pubs:37328
Language:
English

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