Recent advances in visible-light photocatalytic deuteration reactions

Zhou, Rong; Ma, Lishuang; Yang, Xiaona; Cao, Jilei

doi:10.1039/d0qo01299h

Cited by 76 publications

(47 citation statements)

References 120 publications

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“…A rapidly growing number of chemical transformations employs DPZs as photocatalysts [49][50][51][52][53][54][55][56][57][58][59][60][61][62][63]. In 2020, Jiang et al reported a radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes (Scheme 4) [64].…”

Section: Applications In Photoredox Chemistrymentioning

confidence: 99%

Recent Advances of Dicyanopyrazine (DPZ) in Photoredox Catalysis

et al. 2021

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Visible light organophotoredox catalysis has emerged as an invaluable tool for organic synthetic transformations since it works brilliantly in tandem with organic substrates and has been known to create unique chemical environment for organic transformations. Dicyanopyrazine (DPZ), a relatively lesser researched organophotoredox catalyst, has shown great potential through its catalytic activity in organic synthesis and necessitates attention of synthetic community.

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Section: Applications In Photoredox Chemistrymentioning

confidence: 99%

Recent Advances of Dicyanopyrazine (DPZ) in Photoredox Catalysis

et al. 2021

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“…Accordingly, significant advances have been made in the deuteration/tritiation of organic compounds via metal-and photocatalysis. [45][46][47][48][49][50][51][52][53] A notable example is the deuteration and tritiation of aromatic C(sp 2 )-H bond using a homogeneous iron catalyst, reported by the Chirik group. 48 This method shows an orthogonal selectivity to the traditional ortho-directing Crabtree iridium catalyst.…”

Section: Introductionmentioning

confidence: 99%

Photoredox Catalyzed Site-Selective Generation of Carbanions from C(sp3)-H bonds in Amines

Murugesan

Donabauer

Narobe

et al. 2021

Preprint

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The selective activation of sp3 carbon-hydrogen bonds in presence of multiple C¬-H bonds is challenging and remains of supreme importance in chemical research. Herein, we describe the activation of a C(sp3) H bond in 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.

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“…[4][5][6][7][8] In this context, the emergence of photocatalysis has provided enormous opportunities for C-H functionalization through direct photo hydrogen atom transfer (HAT) catalysis or by the synergistic combinations of photoredox with HAT catalysis. [9][10][11][12][13][14][15][16][17][18] Aldehydes, one of the most abundant and readily available feedstocks, are enabled to generate acyl radicals to achieve umpolung reactivity by photo-induced HAT in a step-and atom-economic fashion. [19][20] However, the acceptors of acyl radicals were limited to electron-de cient alkenes and radical trappers containing electron-withdrawing leaving groups, [21][22][23][24][25] to result in an electrophilic radical intermediate to turn over the redox-neutral photocatalytic cycle ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Bromine as a Visible-Light-Mediated Polarity-Reversal Catalyst for the Functionalization of Aldehydes

Wang

Liu

Huang

et al. 2020

Preprint

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Polarity-reversal catalysts enable otherwise sluggish or completely ineffective reactions which are characterized by unfavorable polar effects between radicals and substrates. We herein disclose for the first time that when irradiated by visible light, bromine can behave as a polarity-reversal catalyst. Hydroacylation of vinyl arenes, a three-component cascade transformation and deuteration of aldehydes were each achieved in a metal-free manner without initiators by using N-bromosuccinimide as the precatalyst. Light is essential to generate and maintain the active bromine radical during the reaction process. Another key to success is that HBr can behave as an effective hydrogen-donor to turn over the catalytic cycles.

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Recent advances in visible-light photocatalytic deuteration reactions

Abstract: Deuterated organic compounds have widespread applications in many fields such as medicinal chemistry, mechanistic studies, and quantitative analyses. Traditionally, the incorporation of deuterium atom into organic compounds can be achieved...

Cited by 76 publications

References 120 publications

Recent Advances of Dicyanopyrazine (DPZ) in Photoredox Catalysis

Recent Advances of Dicyanopyrazine (DPZ) in Photoredox Catalysis

Photoredox Catalyzed Site-Selective Generation of Carbanions from C(sp3)-H bonds in Amines

Bromine as a Visible-Light-Mediated Polarity-Reversal Catalyst for the Functionalization of Aldehydes

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