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Synthesis, structural characterization, and reactivity studies of 5-CF3SO3-B10H13.

Emily R Berkeley¹, William C Ewing, Patrick J Carroll

¹Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.

Inorganic Chemistry

|May 3, 2014

Summary

A new isomer of triflate-substituted decaborane, 5-TfO-B10H13, was synthesized in an ionic liquid. This isomerizes from the 6-TfO-B10H13 form at higher temperatures and exhibits unique reactivity, forming carboranes and decaborate salts.

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Published on: November 28, 2016

Area of Science:

Inorganic Chemistry
Boron Chemistry
Organic Synthesis

Background:

Previous synthesis of triflate-substituted decaboranes (TfO-B10H13) typically yielded the 6-TfO-B10H13 isomer in cyclopentane solvent.
Ionic liquids offer unique reaction environments that can influence product distribution and isomerization pathways.

Purpose of the Study:

To investigate the synthesis of triflate-substituted decaboranes in ionic liquids.
To characterize the novel 5-TfO-B10H13 isomer and explore its reactivity.
To understand the isomerization mechanism between 6-TfO-B10H13 and 5-TfO-B10H13.

Main Methods:

Reaction of closo-decahydrodecaborate(2-) with trifluoromethanesulfonic acid in 1-butyl-3-methylimidazolium trifluoromethanesulfonate (bmimOTf).
Experimental and computational studies to elucidate isomerization and reaction mechanisms.
Reactivity studies including deprotonation, reactions with alcohols, olefin hydroboration, and adduct formation.

Main Results:

Exclusive formation of the previously unknown 5-TfO-B10H13 isomer under specific ionic liquid conditions.
Demonstration of isomerization of 6-TfO-B10H13 to 5-TfO-B10H13 above room temperature in bmimOTf.
Characterization of diverse reactivity of 5-TfO-B10H13, including formation of anions, boryl ethers, hydroboration products, and adducts.
Synthesis of triflate-substituted ortho-carboranes and decaborate salts via reactions of the 5-TfO-6,9-(Me2S)2-B10H11 adduct.

Conclusions:

The use of ionic liquids significantly alters the outcome of triflate-substituted decaborane synthesis, favoring a novel isomer.
Temperature-dependent isomerization plays a crucial role in product distribution.
The 5-TfO-B10H13 isomer serves as a versatile precursor for synthesizing new boron-containing compounds, including carboranes and decaborates.