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Title: Mechanistic and Synthetic Studies of Biaryl Birch Reductions
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  more » « less
Award ID(s):
1955758
PAR ID:
10441792
Author(s) / Creator(s):
Date Published:
Journal Name:
Synthesis
Volume:
55
Issue:
05
ISSN:
0039-7881
Page Range / eLocation ID:
707 to 718
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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