Related Experiment Video
Updated: Dec 19, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Electronically Driven Regioselective Iridium-Catalyzed C-H Borylation of Donor-π-Acceptor Chromophores Containing
Florian Rauch1, Johannes Krebs1, Julian Günther1
1Institut für Anorganische Chemie and Institute, for Sustainable Chemistry & Catalysis with Boron (ICB), Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
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(F Xyl)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.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
02:36Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
02:35Regioselectivity of Electrophilic Additions-Peroxide Effect
01:25Radical Anti-Markovnikov Addition to Alkenes: Overview
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
03:08Hydroboration-Oxidation of Alkenes
01:26Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...