A Bulky and Electron-Rich N-Heterocyclic Carbene–Palladium Complex (SIPr)Ph2Pd(cin)Cl: Highly Efficient and Versatile for the Buchwald–Hartwig Amination of (Hetero)aryl Chlorides with (Hetero)aryl Amines at Room Temperature

ACS Catalysis ◽  
2021 ◽  
pp. 9252-9261
Author(s):  
Jia-Sheng Ouyang ◽  
Siqi Liu ◽  
Bendu Pan ◽  
Yaqi Zhang ◽  
Hao Liang ◽  
...  
Keyword(s):  
Room Temperature ◽  
Palladium Complex ◽  
Aryl Chlorides ◽  
Highly Efficient ◽  
Aryl Amines

scholarly journals Room-temperature borylation and one-pot two-step borylation/Suzuki–Miyaura cross-coupling reaction of aryl chlorides

RSC Advances ◽  
2018 ◽  
Vol 8 (25) ◽  
pp. 13643-13648 ◽  
Author(s):  
Hong Ji ◽  
Li-Yang Wu ◽  
Jiang-Hong Cai ◽  
Guo-Rong Li ◽  
Na-Na Gan ◽  
...  
Keyword(s):  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Chlorides ◽  
Highly Efficient ◽  
Cross Coupling Reaction

A highly efficient room-temperature strategy for borylation and one-pot two-step borylation/Suzuki–Miyaura cross-coupling reaction of aryl chlorides have been developed.

scholarly journals Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yanjun Li ◽  
Ziqi Ye ◽  
Yu-Mei Lin ◽  
Yan Liu ◽  
Yumeng Zhang ◽  
...  
Keyword(s):  
Room Temperature ◽  
Sodium Formate ◽  
Bioactive Molecules ◽  
Co Catalyst ◽  
Aryl Chlorides ◽  
Aryl Amine ◽  
Drug Molecules ◽  
Photocatalytic System ◽  
Site Selective ◽  
Environmentally Friendly Method

AbstractDevelopment of practical deuteration reactions is highly valuable for organic synthesis, analytic chemistry and pharmaceutic chemistry. Deuterodehalogenation of organic chlorides tends to be an attractive strategy but remains a challenging task. We here develop a photocatalytic system consisting of an aryl-amine photocatalyst and a disulfide co-catalyst in the presence of sodium formate as an electron and hydrogen donor. Accordingly, many aryl chlorides, alkyl chlorides, and other halides are converted to deuterated products at room temperature in air (>90 examples, up to 99% D-incorporation). The mechanistic studies reveal that the aryl amine serves as reducing photoredox catalyst to initiate cleavage of the C-Cl bond, at the same time as energy transfer catalyst to induce homolysis of the disulfide for consequent deuterium transfer process. This economic and environmentally-friendly method can be used for site-selective D-labeling of a number of bioactive molecules and direct H/D exchange of some drug molecules.

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