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Radical Fragment Coupling Route to Geminal Bis(boronates).
1Laboratoire de Synthèse Organique , CNRS UMR 7652 Ecole Polytechnique , Palaiseau , 91128 Cedex , France.
Organic Letters
|August 25, 2018
Summary
This study introduces a new method for synthesizing geminal bis(boronates) using dithiocarbonates and alkenes. This efficient radical addition creates diverse, highly functional compounds previously difficult to access.
Area of Science:
- Organic Chemistry
- Organoboron Chemistry
Background:
- Geminal bis(boronates) are valuable synthetic intermediates.
- Existing methods for synthesizing functionalized geminal bis(boronates) have limitations.
Purpose of the Study:
- To develop a novel and efficient method for synthesizing highly functionalized geminal bis(boronates).
- To explore the scope and limitations of this new synthetic approach.
Main Methods:
- Radical addition of dithiocarbonates to 1,1-bis(boronyl)-3-butene and related alkenes.
- Characterization of the resulting geminal bis(boronate) products.
Main Results:
- The radical addition proceeds smoothly without fragmentation or hydrogen atom abstraction.
- A wide array of highly functional geminal bis(boronates) were synthesized.
- Access to geminal bis(boronyl) cyclopropanes and tetrahydroquinolines was achieved.
Conclusions:
- This novel radical addition offers a versatile route to complex geminal bis(boronates).
- The method provides access to valuable compounds with polar functional groups unobtainable through other synthetic strategies.
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