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Updated: Dec 15, 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
C-H Activation Based Copper-Catalyzed One-Shot Synthesis of N,O-Bidentate Organic Difluoroboron Complexes
Guangying Tan1, Malte L Schrader1, Constantin Daniliuc1
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
Abstract:
Organic BF2 complexes exhibit characteristics such as large Stokes shift, high quantum yield, strong emission intensity, and robust chemical stability, thereby being extensively used in various applications. Herein, we disclose a novel copper-catalyzed cascade C-H activation/acyloxylation and difluoroboronation of 2-phenylpyridine derivatives, thus providing a straightforward and rapid gateway to a series of N,O-bidentate organic BF2 complexes with excellent photophysical properties. Mechanism studies demonstrate that AgBF4 services as BF2 source and oxidant for this elegant transformation. Most of these BF2 complexes have broad and intense absorption and emission bands, and display bright and intensive blue fluorescence as well as large Stokes shifts.
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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.
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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.