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- W4220790291 abstract "The selective activation of sp3 carbon–hydrogen bonds in the presence of multiple C–H bonds is challenging and remains of supreme importance in chemical research. Late-stage modification of complex molecules via sp3 C–H activation is of high prevalence in organic synthesis. Herein, we describe the activation of a C(sp3)–H bond in the α-position to an amine via a carbanion intermediate. In the presence of several α-amine sites, only one specific position is selectively activated. Applying this protocol, the proposed carbanion intermediate was effectively trapped with different electrophiles such as deuterium (D+), tritium (T+), or carbonyl compounds compiling over 50 examples. Further, this methodology was used to install deuterium or tritium in different drug-derivatives (>10 drugs) at a selected position in a late-stage functionalization. In addition, the protocol is suitable for a gram-scale synthesis, and a detailed mechanistic investigation has been carried out to support our hypothesis." @default.
- W4220790291 created "2022-04-03" @default.
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- W4220790291 date "2022-03-15" @default.
- W4220790291 modified "2023-10-09" @default.
- W4220790291 title "Photoredox-Catalyzed Site-Selective Generation of Carbanions from C(sp<sup>3</sup>)–H Bonds in Amines" @default.
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- W4220790291 doi "https://doi.org/10.1021/acscatal.2c00662" @default.
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