Facile Access to Organostibines via Selective Organic Superbase Catalyzed Antimony‐Carbon Protonolysis

Culvyhouse, Jacob; Unruh, Daniel K.; Lischka, Hans; Aquino, Adelia J. A.; Krempner, Clemens

doi:10.1002/ange.202407822

Title: Facile Access to Organostibines via Selective Organic Superbase Catalyzed Antimony‐Carbon Protonolysis

Journal Article · 30 June 2024 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.202407822 · OSTI ID:2407133

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Department of Chemistry &, Biochemistry Texas Tech University Memorial Dr. &, Boston Lubbock Texas 79409 United States
Department of Mechanical Engineering Texas Tech University Lubbock Texas 79409-1021 United States

Abstract The selective formation of antimony‐carbon bonds via organic superbase catalysis under metal‐ and salt‐free conditions is reported. This novel approach utilizes electron‐deficient stibine, Sb(C ₆ F ₅ ) ₃ , to give upon base‐catalyzed reactions with weakly acidic aromatic and heteroaromatic hydrocarbons access to a range of new aromatic and heteroaromatic stibines, respectively, with loss of C ₆ HF ₅ . Also, the significantly less electron‐deficient stibines, Ph ₂ SbC ₆ F ₅ and PhSb(C ₆ F ₅ ) ₂ smoothly underwent base‐catalyzed exchange reactions with a range of terminal alkynes to generate the stibines of formulae PhSb(C≡CPh) ₂ , and Ph ₂ SbC≡CR [R=C ₆ H ₅ , C ₆ H ₄ ‐NO ₂ , COOEt, CH ₂ Cl, CH ₂ NEt ₂ , CH ₂ OSiMe ₃ , Sb(C ₆ H ₅ ) ₂ ], respectively. These formal substitution reactions proceed with high selectivity as only the C ₆ F ₅ groups serve as a leaving group to be liberated as C ₆ HF ₅ upon formal proton transfer from the alkyne. Kinetic studies of the base‐catalyzed reaction of Ph ₂ SbC ₆ F ₅ with phenyl acetylene to form Ph ₂ SbC≡CPh and C ₆ HF ₅ suggested the empirical rate law to exhibit a first‐order dependence with respect to the base catalyst, alkyne and stibine. DFT calculations support a pathway proceeding via a concerted σ‐bond metathesis transition state, where the base catalyst activates the Sb‐C ₆ F ₅ bond sequence through secondary bond interactions.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: NONE; SC0019094

OSTI ID:: 2407133

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 32 Vol. 136; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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Triphenylborane in Metal-Free Catalysis Mummadi, Suresh; Krempner, Clemens Molecules, Vol. 28, Issue 3 https://doi.org/10.3390/molecules28031340	journal	January 2023

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