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Halide-Coupled Double Electron Transfer with Electron-Rich Diboranes.
Erik Filbeck1, Sebastian Cremer1, Moritz C F Jansen1
1Inorganic Chemistry, Ruprecht-Karls University of Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 20, 2023
Summary
A novel diborane reagent, B₂(μ-hpp)₂(OTf)₂, enables unique double electron transfer and halide transfer reactions. This study synthesizes novel diborylated dienamines, expanding diborane chemistry.
Area of Science:
- Organoboron Chemistry
- Synthetic Organic Chemistry
- Catalysis
Background:
- Diboranes are versatile reagents but often unstable.
- The ditriflato-diborane B₂(μ-hpp)₂(OTf)₂ serves as a stable surrogate for the [B₂(hpp)₂]²⁺ dication.
- This reagent exhibits both electrophilic and nucleophilic properties, enabling metallomimetic chemistry.
Purpose of the Study:
- To report a novel reaction type involving diboranes.
- To synthesize novel diborylated dienamines.
- To elucidate the scope and mechanism of this new reaction motif.
Main Methods:
- Utilized the ditriflato-diborane B₂(μ-hpp)₂(OTf)₂ as a key reagent.
- Investigated reaction pathways involving double electron transfer and halide transfer.
- Characterized the synthesized diborylated dienamines.
Main Results:
- Discovered a novel reaction coupling double electron transfer with halide transfer.
- Successfully synthesized a range of novel diborylated dienamines.
- Elucidated the scope and mechanistic details of this unprecedented reaction.
Conclusions:
- The ditriflato-diborane B₂(μ-hpp)₂(OTf)₂ facilitates a unique synthetic transformation.
- This work expands the synthetic utility of diboranes in organic synthesis.
- The developed methodology provides access to valuable diborylated dienamine compounds.
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