A deprotonation pathway to reactive [B]CH2 boraalkenes

Karel Škoch; Chaohuang Chen; Constantin G. Daniliuc; Gerald Kehr; Gerhard Erker

doi:10.1039/D2DT01193J

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A deprotonation pathway to reactive [B]CH₂ boraalkenes†

Karel Škoch,

‡^a Chaohuang Chen,

^a Constantin G. Daniliuc,

^a Gerald Kehr

^a and Gerhard Erker

*^a

Author affiliations

* Corresponding authors

^a Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
E-mail: erker@uni-muenster.de

Abstract

The BH compounds IMes(Ar^F)BH(NTf₂) (Ar^F: C₆F₅ or FpXyl) were converted to the IMes(Ar^F)B [double bond, length as m-dash] CH₂ boraalkenes in a three step reaction sequence of B-methylation with methyllithium, hydride abstraction and deprotonation. The BCH₂ boraalkenes reacted with elemental sulfur to give a thiaborirane product. They underwent [2+2] cycloaddition reactions with carbon dioxide or sulfur dioxide to give four-membered boron containing heterocycles. The boraalkenes added strongly Lewis acidic boranes at their [double bond, length as m-dash] CH₂ carbon atoms. The corresponding HB(C₆F₅)₂/boraalkene adduct reduced carbon monoxide to a –OCH(C₆F₅)– moiety inside a five-membered heterocycle at the B–CH₂–B template. The boraalkenes reacted with the [(Me₂S)AuCl] reagent to form the corresponding (boraalkene)AuCl complexes.

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Article information

DOI: https://doi.org/10.1039/D2DT01193J
Article type: Paper
Submitted: 16 Apr 2022
Accepted: 18 Apr 2022
First published: 19 Apr 2022

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Dalton Trans., 2022,51, 7695-7704

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A deprotonation pathway to reactive [B]CH₂ boraalkenes

K. Škoch, C. Chen, C. G. Daniliuc, G. Kehr and G. Erker, Dalton Trans., 2022, 51, 7695 DOI: 10.1039/D2DT01193J

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Dalton Transactions