Synthesis of Chiral α-CF3-Substituted Benzhydryls via Cross-Coupling Reaction of Aryltitanates

Andrii Varenikov, Evgeny Shapiro, Mark Gandelman

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We describe a highly efficient approach toward α-CF3-substituted benzhydryls thanks to the employment of organotitanium(IV) based nucleophiles. The use of commercially available anesthetic halothane as a cheap fluorinated building block in a sequential one-pot nickel-catalyzed enantioselective cross-coupling reaction of aryl titanates allowed for the synthesis of chiral α-CF3-substituted benzhydryls in good yields and excellent enantioselectivities. Alternatively, α-CF3-benzyl bromides could be employed under similar conditions to obtain the same family of compounds in higher yields and excellent selectivities. A benzhydryl moiety is a common motif in many biologically active compounds, and their enantioenriched fluorinated analogs should be of great interest in the search for novel drugs and agrochemicals.

Original languageEnglish
Pages (from-to)9386-9391
Number of pages6
JournalOrganic Letters
Issue number23
StatePublished - 4 Dec 2020
Externally publishedYes

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