Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry.
Science
; 363(6429): 838-845, 2019 02 22.
Article
in En
| MEDLINE
| ID: mdl-30792297
ABSTRACT
Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal-type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Science
Year:
2019
Type:
Article
Affiliation country:
United States