Arylcyanation of Styrenes by Photoactive Electron Donor–Acceptor Complexes/Copper Catalysis DOI
Qilong Wu, Xufeng Li, Jie Ma

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7949 - 7955

Published: Sept. 11, 2024

A novel electron donor-acceptor (EDA) complex/copper catalysis model has been proposed for the construction of 2,3-diarylpropionitriles under visible light conditions. The developed protocol proceeds via intermolecular charge transfer between photoactive EDA complex dibutamine (DBA), aryl thianthrenium salts, and trimethylsilyl cyanide (TMSCN), followed by a copper catalytic cycle. UV-vis absorption measurements confirm participation complexes as reactive intermediates. This three-component process smoothly in presence pharmaceutically relevant core structures sensitive functional groups, which offers possibility precise editing drug molecules with important scaffolds.

Language: Английский

Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts DOI

Zhengjun He,

Zhi Li,

Shuo Lai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6652 - 6657

Published: July 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Language: Английский

Citations

7
Pd-Catalyzed Divergent Site-Selective Difluoromethylation and Difluoromethylcarbonylation of Aryl Sulfonium Salts DOI

Xujuan Jiang,

Wenbo Gong,

Xiaoxun Li

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 13557 - 13566

Published: Aug. 28, 2024

The incorporation of the difluoromethyl (CF2H) group into arenes has increasingly been recognized as important in drug discovery. Herein, we report a divergent cross-coupling method for constructing both aryl difluoromethanes and difluoroketones from thianthrenium salts. Site selectivity Negishi-type coupling C1 insertion reactions was achieved under palladium catalysis. Both transformations proceed with broad functional tolerance, enabling late-stage difluoromethylation difluoromethylcarbonylation complex molecules. synthetic utility this demonstrated by synthesizing four pharmaceutical analogues same precursor applying it downstream functionalization difluoroketones.

Language: Английский

Citations

7
Difluoromethyl phenoxathiinium salt: A new general and versatile difluoromethylating reagent with divergent ·CF2H, CF2H+, and:CF2 reactivities DOI

Yuan-Qing Gu,

Hong-Xin Long,

Dandan Zhang

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(3), P. 953 - 962

Published: Dec. 27, 2023

Language: Английский

Citations

13
Pd-catalyzed relay Heck arylation of alkenyl alcohols with arylsulfonium salts DOI

Jiawei Song,

Xia Fang,

Xiulan Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4219 - 4230

Published: Jan. 1, 2024

The Pd-catalyzed relay Heck arylation of alkenyl alcohols with arylsulfonium salts is first reported for synthesizing arylalkyl ketones or aldehydes.

Language: Английский

Citations

5
Arylcyanation of Styrenes by Photoactive Electron Donor–Acceptor Complexes/Copper Catalysis DOI
Qilong Wu, Xufeng Li, Jie Ma

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7949 - 7955

Published: Sept. 11, 2024

A novel electron donor-acceptor (EDA) complex/copper catalysis model has been proposed for the construction of 2,3-diarylpropionitriles under visible light conditions. The developed protocol proceeds via intermolecular charge transfer between photoactive EDA complex dibutamine (DBA), aryl thianthrenium salts, and trimethylsilyl cyanide (TMSCN), followed by a copper catalytic cycle. UV-vis absorption measurements confirm participation complexes as reactive intermediates. This three-component process smoothly in presence pharmaceutically relevant core structures sensitive functional groups, which offers possibility precise editing drug molecules with important scaffolds.

Language: Английский

Citations

5