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Issue 18, 2020
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δ-Cyano substituted para-quinone methides enable access to unsymmetric tri- and tetraarylmethanes containing all-carbon quaternary stereocenters

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Abstract

para-Quinone methides bearing an electron-withdrawing cyano group at the exocyclic methylene δ-position were identified as valuable 1,6-conjugate addition building blocks for acyclic all-carbon quaternary stereocenter construction. A wide variety of electron-rich arenes as nucleophiles were tolerated, effectively furnishing diverse unsymmetrical triarylmethanes bearing all-carbon quaternary stereocenters. The robust transformable abilities of the cyano group provide a platform to access other valuable functional group-containing unsymmetrical tri- and tetraarylmethanes that are otherwise difficult to be prepared. Computational studies supported the hypothesis that the cyano group at the δ-position tunes the molecular electron-density distribution, and the stability of para-quinone methides is enhanced by lowering their polymerizability.

Graphical abstract: δ-Cyano substituted para-quinone methides enable access to unsymmetric tri- and tetraarylmethanes containing all-carbon quaternary stereocenters

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Article information


Submitted
14 Mar 2020
Accepted
17 Apr 2020
First published
25 Apr 2020

Org. Biomol. Chem., 2020,18, 3522-3526
Article type
Paper

δ-Cyano substituted para-quinone methides enable access to unsymmetric tri- and tetraarylmethanes containing all-carbon quaternary stereocenters

Y. Qi, F. Zhang, L. Wang, A. Feng, R. Zhu, S. Sun, W. Li and L. Liu, Org. Biomol. Chem., 2020, 18, 3522
DOI: 10.1039/D0OB00551G

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