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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 22
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Synthetic Communications Reviews

Regioselective lithiation of benzyl imidazole: Synthesis and evaluation of new organocatalysts for trans-diol functionalization.

Mohamed El-MansyChemistry Department, Oregon State University, Corvallis, OR, USA; ;Organometallic and Organometalloid Chemistry Department, National Research Centre, Cairo, EgyptORCID Iconhttp://orcid.org/0000-0001-9701-6516View further author information
ORCID Icon,
Ankan GhoshChemistry Department, Oregon State University, Corvallis, OR, USA; View further author information
,
Paul Ha-Yeon CheongChemistry Department, Oregon State University, Corvallis, OR, USA; View further author information
&
Rich CarterChemistry Department, Oregon State University, Corvallis, OR, USA; Correspondence[email protected]
ORCID Iconhttp://orcid.org/0000-0002-9100-1791View further author information
ORCID Icon
Pages 3131-3139 | Received 27 Jun 2019, Published online: 30 Aug 2019
 
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Abstract

Benzyl imidazole was successfully lithiated using n-BuLi at −78 °C and verified by deuterium incorporation. The chemical reaction of the lithiated benzimidazole was explored with a series of different electrophiles. This approach was utilized to synthesize new anti and syn diphenyl organocatalysts for trans-diol functionalization.

Graphical Abstract

Acknowledgments

Prof. Claudia Maier (OSU) and Jeff Morré (OSU) are acknowledged for mass spectra data. Drs. Ryne Johnston and Maduka Ogba are acknowledged for the early work on the computational analysis of the Tan chemistry.

Disclosure statement

No competing financial interests have been declared.

Additional information

Funding

Financial support provided by the National Science Foundation [CHE-1665246] and Oregon State University.

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