Dioxygen compatible electron donor-acceptor catalytic system and its enabled aerobic oxygenation DOI Creative Commons
Jialiang Wei,

Junhong Meng,

Caifang Zhang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Feb. 29, 2024

Abstract The photochemical properties of Electron Donor-Acceptor (EDA) complexes present exciting opportunities for synthetic chemistry. However, these strategies often require an inert atmosphere to maintain high efficiency. Herein, we develop EDA complex photocatalytic system through rational design, which overcomes the oxygen-sensitive limitation traditional systems and enables aerobic oxygenation reactions dioxygen activation. mild oxidation transfers electrons from donor effective catalytic acceptor upon visible light irradiation, are subsequently captured by molecular oxygen form superoxide radical ion, as demonstrated specific fluorescent probe, dihydroethidine (DHE). Furthermore, this visible-light mediated oxidative protocol is successfully applied in boronic acids. We believe that activation strategy enabled not only provides a practical approach but also promotes design application photocatalysis under ambient conditions.

Language: Английский

Sodium Dithionite‐Mediated Decarboxylative Sulfonylation: Facile Access to Tertiary Sulfones DOI
Yaping Li, Shihao Chen, Ming Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(23), P. 8907 - 8911

Published: March 9, 2020

Abstract A straightforward multicomponent decarboxylative cross coupling of redox‐active esters (N‐hydroxyphthalimide ester), sodium dithionite, and electrophiles was established to construct sterically bulky sulfones. The inorganic salt dithionite not only served as the sulfur dioxide source, but also acted an efficient radical initiator for decarboxylation. Notably, diverse naturally abundant carboxylic acids artificially prepared carboxyl‐containing drugs with multiple heteroatoms sensitive functional groups successfully underwent this sulfonylation provide tertiary Mechanistic studies further demonstrated that decarboxylation rate‐determining step occurred via a single‐electron transfer (SET) process assistance dithionite.

Language: Английский

Citations

136

Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions DOI

Kai-Jian Liu,

Ji-Hui Deng,

Jie Yang

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 22(2), P. 433 - 438

Published: Nov. 26, 2019

The first example of selective oxidation sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established. desired products could be easily collected through recrystallization in large-scale preparation.

Language: Английский

Citations

125

Synergistic cooperative effect of CF3SO2Na and bis(2-butoxyethyl)ether towards selective oxygenation of sulfides with molecular oxygen under visible-light irradiation DOI

Kai-Jian Liu,

Zheng Wang,

Linghui Lu

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 23(1), P. 496 - 500

Published: Nov. 26, 2020

A practical method for the switchable synthesis of sulfoxides and sulfones through visible-light-initiated CF3SO2Na/2-butoxyethyl ether synergistic catalyzed oxygenation sulfides was developed.

Language: Английский

Citations

100

Ethylene Glycol: A Green Solvent for Visible Light‐Promoted Aerobic Transition Metal‐Free Cascade Sulfonation/Cyclization Reaction DOI

Yuqin Jiang,

Jing Li,

Zhi‐Wen Feng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(13), P. 2609 - 2614

Published: May 1, 2020

Abstract With ethylene glycol as a green solvent, general transition metal‐free photocatalytic system using 9‐mesityl‐10‐methylacridinium perchlorate (Acr + −Mes ⋅ ClO 4 − ) catalyst was developed for the synthesis of sulfone‐containing heterocycles including thioflavones, oxindoles, and quinoline‐2,4(1 H ,3 )‐diones through cascade sulfonation/cyclization reactions under irradiation blue light at room temperature. magnified image

Language: Английский

Citations

78

General sulfone construction via sulfur dioxide surrogate control DOI
Shihao Chen, Yaping Li, Ming Wang

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 22(2), P. 322 - 326

Published: Dec. 5, 2019

A highly efficient one-step synthesis of alkyl–alkyl and aryl–alkyl sulfones with tuneable masked “SO2” sources is described.

Language: Английский

Citations

76

Recyclable Perovskite as Heterogeneous Photocatalyst for Aminomethylation of Imidazo‐Fused Heterocycles DOI
Tao Shi, Kai Sun, Xiaolan Chen

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(11), P. 2143 - 2149

Published: Jan. 8, 2020

Abstract A sustainable and cost‐effective protocol for direct aminomethylation of imidazo‐fused heterocycles by decarboxylative coupling reaction N ‐phenylglycines with in the presence CsPbBr 3 under irradiation visible light has been developed. This is first example ‐catalyzed heterocycles. The eminent advantage this work that, easily prepared can be used at least 5 times without obvious reduction its activity, exhibiting high catalyst economic feature. magnified image

Language: Английский

Citations

75

Electrochemical Oxidation Enables Regioselective and Scalable α-C(sp3)-H Acyloxylation of Sulfides DOI
Huamin Wang, Meng He, Yongli Li

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(9), P. 3628 - 3637

Published: Feb. 26, 2021

A highly selective, environmentally friendly, and scalable electrochemical protocol for the construction of α-acyloxy sulfides, through synergistic effect self-assembly-induced C(sp3)–H/O–H cross-coupling, is reported. It features exceptionally broad substrate scope, high regioselectivity, gram-scale synthesis, complex molecules, applicability to a variety nucleophiles. Moreover, soft X-ray absorption technique series control experiments have been utilized demonstrate pivotal role self-assembly substrates, which indeed responsible excellent compatibility precise regioselectivity in our protocol.

Language: Английский

Citations

74

Incorporating Photochromic Triphenylamine into a Zirconium–Organic Framework for Highly Effective Photocatalytic Aerobic Oxidation of Sulfides DOI

Xin-Nan Zou,

De-Shan Zhang, Tian‐Xiang Luan

et al.

ACS Applied Materials & Interfaces, Journal Year: 2021, Volume and Issue: 13(17), P. 20137 - 20144

Published: April 22, 2021

A zirconium-based metal–organic framework (MOF) was successfully constructed via solvothermal assembly of a triphenylamine-based tricarboxylate ligand and Zr(IV) salt, the structure simulation which revealed that it possesses two-dimensional layered with relatively rare dodecnuclear Zr12 cluster as inorganic building unit. The inherent photo-responsive property derived from incorporated photochromic triphenylamine groups combined its high stability makes MOF an efficient heterogeneous photocatalyst for oxidation sulfides, is fundamentally important reaction type in both environmental pharmaceutical industries. photocatalytic activity first investigated under various conditions thioanisole representative sulfide substrate. exhibited efficiency selectivity on aerobic methanol utilizing molecular oxygen air oxidant blue light irradiation 10 h. Its performance also observed when extending substrate to diverse derivatives even sulfur-containing nerve agent simulant (2-chloroethyl ethyl sulfide). broad set substrates make triphenylamine-incorporating highly promising photocatalyst.

Language: Английский

Citations

74

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis DOI

Qiuli Yan,

Wenwen Cui, Xiuyan Song

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(9), P. 3663 - 3668

Published: April 21, 2021

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used the photocatalytic transformation. Diverse organosulfones were obtained moderate to good yields. This strategy demonstrates promising approach toward synthesis diverse and useful organosulfones.

Language: Английский

Citations

68

Stepwise benzylic oxygenation via uranyl-photocatalysis DOI
Deqing Hu, Xuefeng Jiang

Green Chemistry, Journal Year: 2021, Volume and Issue: 24(1), P. 124 - 129

Published: Dec. 13, 2021

Stepwise oxygenation of benzylic molecules with uranyl photocatalysis was realized under ambient conditions. The accuracy the stepwise ensured by tunability redox potential in through solvents and additives.

Language: Английский

Citations

57