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Synthesis 2023; 55(05): 707-718
DOI: 10.1055/s-0042-1751387
DOI: 10.1055/s-0042-1751387
short review
Mechanistic and Synthetic Studies of Biaryl Birch Reductions
This work was partly supported by the US National Science Foundation (CHE-1955758).
Abstract
The Birch reduction of biaryls generally converts one of the two arenes into a cyclohexa-1,4-diene. Biaryls are more reactive than monocyclic arenes under the Birch conditions. Unlike the reduction of monocyclic arenes, biaryl reduction proceeds through two consecutive electron transfer steps before the protonation of the dianion intermediate. The biaryl reductions and subsequent alkylations in one pot rapidly increase the molecular complexity and thus have been used in the synthesis of natural products and drug-like molecules.
1 Introduction
2 The Physical Organic Chemistry of the Birch Reduction of Biaryls
3 Biaryls as the Mediators of Electron Transfer
4 Methods for the Dissolving-Metal Reduction of Biaryls
5 Intercepting the Biaryl Reduction Intermediates with Electrophiles
6 Synthetic Applications of the Dissolving-Metal-Mediated Reductions of Biaryls
7 Outlook
Publikationsverlauf
Eingereicht: 30. August 2022
Angenommen nach Revision: 27. Oktober 2022
Artikel online veröffentlicht:
22. November 2022
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