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Transition-metal free boron triiodide-mediated reduction of nitroarenes from simple borohydride reagents

09 October 2023, Version 3
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The reduction of nitroarenes using KBH4 and I2 is described. BI3 is generated in situ, which was shown to be the active reductant. Conditions were optimized for BI3 generation, and then applied to a wide range of nitroarenes, including traditionally challenging substrates. The method constitutes a practical reduction option which produces low toxicity boric acid and potassium iodide upon workup.

Keywords

Nitroarene reduction
boron chemistry

Supplementary materials

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Description
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Supplementary Info
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Reaction protocols and spectroscopic characterization data
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Version History

Oct 09, 2023 Version 3

Version Notes

Updated Proposed Mechanism of Action, small wording changes.

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-q5r9g-v3
D O I: 10.26434/chemrxiv-2023-q5r9g-v3 [opens in a new tab]

Funding

National Science Foundation
NSF Career Award CHE 2239556

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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