Electronically Driven Regioselective Iridium‐Catalyzed C−H Borylation of Donor‐π‐Acceptor Chromophores Containing Triarylboron Acceptors

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Abstract: We observed a surprisingly high electronically driven regioselectivity for the iridium‐catalyzed C−H borylation of donor‐π‐acceptor (d‐π‐A) systems with diphenylamino (1) or carbazolyl (2) moieties as the donor, bis (2,6‐bis (trifluoromethyl) phenyl) boryl (B (FXyl) 2) as the acceptor, and 1,4‐phenylene as the π‐bridge. Under our conditions, borylation was observed only at the sterically least encumbered para‐positions of the acceptor group. As boronate esters are versatile building blocks for organic synthesis (C−C coupling, functional group transformations) the C−H borylation represents a simple potential method for post‐functionalization by which electronic or other properties of d‐π‐A systems can be fine‐tuned for specific applications. The photophysical and electrochemical properties of the borylated (1‐(Bpin) 2) and unborylated (1) diphenylamino‐substituted d‐π‐A systems were investigated. Interestingly, the borylated derivative exhibits coordination of THF to the boronate ester moieties, influencing the photophysical properties and exemplifying the non‐innocence of boronate esters.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Electronically Driven Regioselective Iridium‐Catalyzed C−H Borylation of Donor‐π‐Acceptor Chromophores Containing Triarylboron Acceptors ; volume:26 ; number:46 ; year:2020 ; pages:10626-10633 ; extent:8
Chemistry - a European journal ; 26, Heft 46 (2020), 10626-10633 (gesamt 8)

Creator: Rauch, Florian
Krebs, Johannes
Günther, Julian
Friedrich, Alexandra
Hähnel, Martin
Krummenacher, Ivo
Braunschweig, Holger
Finze, Maik
Marder, Todd B.

DOI: 10.1002/chem.202002348

URN: urn:nbn:de:101:1-2022060308113819946909

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:27 AM CEST

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Electronically Driven Regioselective Iridium‐Catalyzed C−H Borylation of Donor‐π‐Acceptor Chromophores Containing Triarylboron Acceptors

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