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Borole formation by 1,1-carboboration.
Fang Ge1, Gerald Kehr, Constantin G Daniliuc
1Organisch-Chemisches Institut, Universität Münster , Corrensstrasse 40, D-48149 Münster, Germany.
Journal of the American Chemical Society
|December 21, 2013
Summary
Researchers synthesized novel boroles from silylethynylboranes and a Lewis acid. These boroles can be stabilized or undergo cycloaddition reactions, expanding synthetic possibilities in organoboron chemistry.
Area of Science:
- Organometallic Chemistry
- Boron Chemistry
- Synthetic Organic Chemistry
Background:
- Boroles are heterocyclic compounds containing boron, with applications in materials science and catalysis.
- The synthesis of novel borole derivatives remains an active area of research, seeking new structures and reactivity.
- Lewis acid-mediated reactions offer pathways to construct complex boron-containing heterocycles.
Purpose of the Study:
- To synthesize and characterize new borole compounds derived from silylethynylboranes.
- To investigate the reactivity of these novel boroles, including stabilization and cycloaddition reactions.
- To explore the utility of tris(pentafluorophenyl)borane as a Lewis acid in borole synthesis.
Main Methods:
- Reaction of bis(trimethylsilylethynyl)diphenylaminoborane with tris(pentafluorophenyl)borane (B(C6F5)3) at ambient temperature.
- Stabilization of the resulting borole via adduct formation with pyridine.
- Reaction of bis(trimethylsilylethynyl)phenylborane with B(C6F5)3 followed by treatment with 3-hexyne.
Main Results:
- The reaction yielded the target borole (9) along with a minor thermal follow-up product (12).
- Borole 9 was successfully stabilized as a pyridine adduct (10).
- A separate reaction produced borole 14, which underwent a [4 + 2] cycloaddition with 3-hexyne to yield product 15.
Conclusions:
- Novel borole structures were synthesized using a Lewis acid-mediated approach.
- The synthesized boroles demonstrate tunable reactivity, allowing for stabilization or participation in cycloaddition reactions.
- This study expands the synthetic toolbox for accessing functionalized organoboron heterocycles.
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