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(searched for: doi:10.1038/s42004-021-00513-2)
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Stephen G. Davey
Published: 1 June 2021
Nature Reviews Chemistry, Volume 5, pp 368-368; doi:10.1038/s41570-021-00294-1

Abstract:
A range of aryl and alkenyl organosodium reagents can be prepared by halogen–sodium exchange reactions with neopentylsodium and may be a useful alternative to widely used organolithium reagents.
, , Pinaki Bhusan De
Published: 9 April 2021
Synthesis; doi:10.1055/a-1478-7061

Abstract:
This short review describes the recent emergence of organosodium chemistry, motivated by the requirements of modern synthetic chemistry for sustainability, and powered by the use of sodium dispersion, a form of sodium that is commercially available, easy to handle, and has a large active surface area. We present recent methods for the preparation of organosodium compounds using sodium dispersion, and their applications to synthesis. Sodium amides and phosphides are also briefly discussed. 1 Introduction 2 Sodium Dispersion 3 Preparation of Organosodium Compounds 3.1 Two-Electron Reduction of Aryl Halides 3.2 Halogen–Sodium Exchange 3.3 Directed Metalation 3.4 Cleavage of C–C and C–Heteroatom Bonds 4 Synthetic Applications 4.1 Reduction in Combination with a Proton Source 4.1.1 Bouveault–Blanc Reduction 4.1.2 Birch Reduction 4.1.3 Reductive Deuteration 4.1.4 Chemoselective Cleavage of Amides and Nitriles 4.2 Difunctionalization of Alkenes and Alkynes 5 Sodium Amides and Phosphides 6 Conclusions and Outlook
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