Journal Article

PUBDB-2026-00670

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Complete Series of 1,2‐Bis(trihalogenosilyl)benzenes (F, Cl, Br, I): A Platform for Cooperating Lewis‐Acidic Sites in Close Quarters

Schmidt, M.Extern* ; Hürtgen, N. H. H. ; Virovets, A.Extern* ; Lerner, H.-W. ; Wagner, M. (Corresponding author)Extern*

2026
Wiley-VCH Weinheim

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Please use a persistent id in citations: doi:10.1002/zaac.202500154  doi:10.3204/PUBDB-2026-00670

Abstract: 1,2-Bis(trihalogenosilyl)benzenes are versatile synthetic building blocks and represent a unique class of ditopic Lewis acids. Building on the recently reported compound 1,2-(Cl3Si)2C6H2Me2 (1Cl; Me groups in 4,5-positions), the practical synthetic access to its sixfold fluorinated (1F), brominated (1Br), and iodinated (1I) congeners is disclosed. Compound 1F is obtained via Cl/F exchange on 1Cl using SbF3 (71%). The synthesis of 1Br involves a [4 + 2]-cycloaddition reaction between Br3SiC≡CSiBr3 and 2,3-dimethyl-1,3-butadiene to furnish the corresponding 1,4-cyclohexadiene, which is subsequently dehydrogenated and aromatized using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (overall 59%). Compound 1I is formed through H/I exchange on 1,2-(H3Si)2-C6H2Me2 with BI3 (32%). All species 1F−1I are comprehensively characterized by NMR spectroscopy, X-ray crystallography, elemental analysis, and high-resolution mass spectrometry. Moreover, adducts of 1F with either 1 equiv. or 2 equiv. of F− are shown to form an inverse chelate featuring a Si−(μ-F)−Si′ bridge or a mixed bridging/terminal coordination motif, respectively.

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Contributing Institute(s):

1. FS DOOR-User (FS DOOR-User)

Research Program(s):

1. 6G3 - PETRA III (DESY) (POF4-6G3) (POF4-6G3)
2. FS-Proposal: I-20220822 (I-20220822) (I-20220822)
3. FS-Proposal: R-20240674 (R-20240674) (R-20240674)

Experiment(s):

1. PETRA Beamline P24 (PETRA III)

Appears in the scientific report 2026

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Database coverage:
; ; ; Clarivate Analytics Master Journal List ; Current Contents - Physical, Chemical and Earth Sciences ; DEAL Wiley ; Ebsco Academic Search ; Essential Science Indicators ; IF < 5 ; JCR ; Nationallizenz ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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