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Yanan Wu

Bio: Yanan Wu is an academic researcher from Nanjing University. The author has contributed to research in topics: Chemistry & Combinatorial chemistry. The author has an hindex of 3, co-authored 3 publications receiving 41 citations.

Papers
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Journal ArticleDOI
TL;DR: Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate inalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic Aziridines.

36 citations

Journal ArticleDOI
TL;DR: A redox-neutral P( O)-N coupling reaction of P(O)-H compounds with azides via photoredox and copper catalysis is reported, providing new access to useful phosphinamides, phosphonamide, and phosphoramides.

19 citations

Journal ArticleDOI
TL;DR: A synthetic strategy with the visible-light photo-catalytic synergistic combination of electron and energy transfer processes has been developed for the multicomponent synthesis of β-arylsulfonyl(diarylphosphinoyl)-α,α-diarylethyl-amines from readily available arylsulfinic acids.

15 citations

Journal ArticleDOI
TL;DR: In this paper , a mild, metal-free method was developed for synthesizing 2-substituted quinazolinones in good to excellent yields (50% to 99%) from methyl 2-aminobenzoates or 2aminobenzamides using 2,2,2-trichloroethyl imidates hydrochloride as the organic synthon.

3 citations

Journal ArticleDOI
TL;DR: In this paper , an S(O)2-N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis was developed.
Abstract: We here have developed an S(O)2–N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the nitrogen nucleophilic substitution reactions. Significantly, this transformation intends to utilize the property of visible light-induced azides to generate triplet nitrene and followed coupling with sulfonyl radicals in situ to achieve structurally diverse benzenesulfinamides in good yields.

Cited by
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Journal ArticleDOI
TL;DR: In this paper, the authors present a review of the recent developments in the field of late stage functionalization of complex biorelevant compounds and highlight the expected future progress and potential applications.
Abstract: The late stage functionalization (LSF) of complex biorelevant compounds is a powerful tool to speed up the identification of structure-activity relationships (SARs) and to optimize ADME profiles. To this end, visible-light photocatalysis offers unique opportunities to achieve smooth and clean functionalization of drugs by unlocking site-specific reactivities under generally mild reaction conditions. This review offers a critical assessment of current literature, pointing out the recent developments in the field while emphasizing the expected future progress and potential applications. Along with paragraphs discussing the visible-light photocatalytic synthetic protocols so far available for LSF of drugs and drug candidates, useful and readily accessible synoptic tables of such transformations, divided by functional groups, will be provided, thus enabling a useful, fast, and easy reference to them.

167 citations

Journal ArticleDOI
TL;DR: Mechanism studies suggest a previous elusive energy transfer pathway from photocatalyst to N-heteroarenes and oxidants is suggested.

58 citations

Journal ArticleDOI
TL;DR: In this article, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3 )-N, N=S, and N=P bond formation are described.
Abstract: Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3 )-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C-H amidations strategies, an intermolecular regioselective C-H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.

45 citations

Journal ArticleDOI
Yi-Dan Du1, Cong-Ying Zhou1, Wai-Pong To1, Hai-Xu Wang1, Chi-Ming Che1 
TL;DR: Mechanistic studies revealed that iron porphyrin plays a dual role as a photosensitizer and as a catalyst giving rise to a reactive iron–nitrene intermediate for subsequent C–N bond formation.
Abstract: Visible light driven nitrene transfer and insertion reactions of organic azides are an attractive strategy for the design of C–N bond formation reactions under mild reaction conditions, the challenge being lack of selectivity as a free nitrene reactive intermediate is usually involved. Herein is described an iron(III) porphyrin catalysed sp3 C–H amination and alkene aziridination with selectivity by using organic azides as the nitrogen source under blue LED light (469 nm) irradiation. The photochemical reactions display chemo- and regio-selectivity and are effective for the late-stage functionalization of natural and bioactive compounds with complexity. Mechanistic studies revealed that iron porphyrin plays a dual role as a photosensitizer and as a catalyst giving rise to a reactive iron–nitrene intermediate for subsequent C–N bond formation.

40 citations

Journal ArticleDOI
Yeongyu Hwang1, Hoimin Jung1, Euijae Lee1, Dong-Wook Kim1, Sukbok Chang1 
TL;DR: A new catalytic platform is established for the unique lactam formation, leading to the unprecedented chemoselective reactivity (up to >20:1) towards a diverse array of competing sites, such as tertiary, secondary, benzylic, allylic C-H bonds and aromatic π-system.
Abstract: The transition-metal-catalyzed nitrenoid transfer reaction is one of the most attractive methods for installing a new C-N bond into diverse reactive units. While numerous selective aminations are known, understanding complex structural effects of the key intermediates on the observed chemoselectivity is still elusive in most cases. Herein, we report a designing approach to enable selective nitrenoid transfer leading to sp2 spirocyclization and sp3 C-H insertion by cooperative two-point modulation of ligands in the CpXIr(III)(κ2-chelate) catalyst system. Computational analysis led us to interrogate structural motifs that can be attributed to the desired mechanistic dichotomy. Multivariate linear regression analysis on the perturbation on the η5-cyclopentadienyl ancillary (CpX) and LX coligand, wherein we prepared over than 40 new catalysts for screening, allowed for construction of an intuitive yet robust statistical model that predicts a large set of chemoselective outcomes, implying that the catalysts' structural effects play a critical role on the chemoselective nitrenoid transfer. On the basis of this quantitative analysis, a new catalytic platform is now established for the unique lactam formation, leading to the unprecedented chemoselective reactivity (up to >20:1) toward a diverse array of competing sites, such as tertiary, secondary, benzylic, allylic C-H bonds, and aromatic π system.

36 citations