Titanium(IV)-Mediated Ring-Opening/Dehydroxylative Cross-Coupling of Diaryl-Substituted Methanols with Cyclopropanol Derivatives.

J Org Chem

Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

Published: November 2021

AI Article Synopsis

  • A new method using titanium(IV) facilitates the reaction of diaryl-substituted methanols and cyclopropanol derivatives, leading to the formation of γ,γ-diaryl esters.
  • These reactions are effective and yield moderate to good results, making them valuable for synthetic applications.
  • The resulting esters can be used to modify complex molecules from drugs like fenofibrate and isoxepac, as well as in synthesizing a precursor for the antidepressant Zoloft.

Article Abstract

A titanium(IV)-mediated ring-opening/dehydroxylative cross-coupling of diaryl-substituted methanols with a cyclopropanol derivative was developed. The reactions proceeded efficiently to provide synthetically useful γ,γ-diaryl esters in moderate to good yields, which could be applied to the functionalization of complex molecules derived from bioactive fenofibrate and isoxepac and the synthesis of a precursor of Zoloft.

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Source
http://dx.doi.org/10.1021/acs.joc.1c01790DOI Listing

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