Hydroxymethyl‐Substituted Tetrathiatriarylmethanol with Variable Reactivity: Selective Access to Three Different Trityl Radicals by Unique Acid‐Mediated Reactions

Author:

Gao Yande1,Feng Meirong1,Gao Longfei1,Leng Yurui1,Han Guifang1,Song Yuguang1,Liu Yangping1ORCID

Affiliation:

1. Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy Tianjin Medical University Tianjin 300070 P. R. China

Abstract

AbstractTetrathiatriarylmethyl radicals have found wide applications in electron paramagnetic resonance (EPR) spectroscopy and imaging as well as dynamic nuclear polarization (DNP). Recently, intense effort has been devoted to the derivatization of trityl radicals, but there is still a lack of highly efficient methods for access to these radicals. Herein, we report novel acid‐mediated protocols for straightforward and selective synthesis of the hydroxymethyl, aldehyde and methyl derivatives of trityl radicals from the sole substrate hydroxymethyl‐substituted tetrathiatriarylmethanol. The resulting trityl radicals exhibit various redox properties as shown by their cyclic voltammetric results. Importantly, the use of these protocols enables site‐specific deuteration of the three trityl radicals, which show unique EPR spectral properties. Overall, our study reveals the crucial effect of the acids on the synthesis of these trityl radicals and provides a new approach for selective access to different trityl radicals, thus enriching their synthetic chemistry.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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