Abnormal Tin–Boron Exchange in the Attempted Synthesis of a Borylated Borole. Issue 64 (25th October 2017)

• Record Type: Journal Article
• Authors: Braunschweig, Holger; Dömling, Michael; Kachel, Stephanie; Kelch, Hauke; Kramer, Thomas; Krummenacher, Ivo; Lenczyk, Carsten; Lin, Shujuan; Lin, Zhenyang; Possiel, Christian; Radacki, Krzysztof
• Is Part Of: Chemistry. Volume 23:Issue 64(2017)
• Page Start: 16167
• Page End: 16170
• Publication Date: 2017-10-25
• Subjects: boranes -- elimination -- heterocycles -- multiple bonds -- tin; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201703810
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Boroles are important motifs within functional materials. With the aim to prepare a pinacolboryl‐substituted derivative, the metallacycle transfer from corresponding zirconium and tin precursors has been explored. We show that the reaction of 1, 1‐dimethyl‐2, 3, 4, 5‐tetrapinacolborylstannole with dichloro(phenyl)borane does not provide the desired borole, but instead a stannyl‐substituted 1‐chloroboracyclopent‐3‐ene. Spectroscopic and structural details of this highly functionalized boracycle indicate that intramolecular interactions between the tin and oxygen atoms of the boryl substituents may account for the unexpected outcome of the tin‐boron exchange reaction. Abstract : Don′t be a stannole ! The tin–boron exchange reaction of 1, 1‐dimethyl‐2, 3, 4, 5‐tetrapinacolborylstannole with dichloro(phenyl)borane was shown to give a stannyl‐substituted 1‐chloroboracyclopent‐3‐ene instead of the desired borole (see graphic). Spectroscopic and structural properties of this highly functionalized boracycle are presented together with initial results of its reactivity.