Organotitanium nucleophiles in asymmetric cross-coupling reaction: Stereoconvergent synthesis of chiral α-cf3 thioethers

Andrii Varenikov, Mark Gandelman

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

Asymmetric Ni-catalyzed cross-coupling reactions have become a very attractive tool for the stereoselective construction of valuable organic chiral materials. While various nucleophiles are used in such transformation, organotitanium(IV) has not been used before. Herein we demonstrate, for the first time, that organotitanium species can serve as efficient coupling partners in asymmetric cross-couplings, which have proven to be beneficial, compared to the commonly used organomagnesium and organozinc counterparts. This principle is exemplified by the first asymmetric catalytic synthesis of CF3-substituted thioethers via a Ni-catalyzed stereoconvergent cross-coupling reaction. Thioether moieties and their derivatives are common motifs in many biologically active compounds, and their enantioenriched fluorinated analogs should be of great interest in the search for novel drugs and agrichemicals.

Original languageEnglish
Pages (from-to)10994-10999
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number28
DOIs
StatePublished - 17 Jul 2019
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

Funding

The authors acknowledge financial support from the Israel Science Foundation (grant no. 1890_/15). We are grateful to Dr. Natalia Fridman for the X-ray analysis and structure solution of compounds 2s and 15a .

FundersFunder number
Israel Science Foundation1890_/15

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