Unparalleled Rates for the Activation of Aryl Chlorides and Bromides: Coupling with Amines and Boronic Acids in Minutes at Room Temperature

2002 ◽  
Vol 114 (24) ◽  
pp. 4940-4942 ◽  
Author(s):  
James P. Stambuli ◽  
Ryoichi Kuwano ◽  
John F. Hartwig
Keyword(s):  
Room Temperature ◽  
Boronic Acids ◽  
Aryl Chlorides

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

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.

scholarly journals A convenient catalyst system for microwave accelerated cross-coupling of a range of aryl boronic acids with aryl chlorides

2007 ◽  
Vol 3 ◽  
Author(s):  
Matthew L Clarke ◽  
Marcia B France ◽  
Jose A Fuentes ◽  
Edward J Milton ◽  
Geoffrey J Roff
Keyword(s):  
Cross Coupling ◽  
Catalyst System ◽  
Boronic Acids ◽  
Aryl Chlorides

Chan–Lam-Type S-Arylation of Thiols with Boronic Acids at Room Temperature

2012 ◽  
Vol 77 (6) ◽  
pp. 2878-2884 ◽  
Author(s):  
Hua-Jian Xu ◽  
Yong-Qiang Zhao ◽  
Teng Feng ◽  
Yi-Si Feng
Keyword(s):  
Room Temperature ◽  
Boronic Acids

Room temperature Pd(0)/Ad3P-catalyzed coupling reactions of aryl chlorides with bis(pinacolato)diboron

2019 ◽  
Vol 60 (11) ◽  
pp. 760-763 ◽  
Author(s):  
Jie Dong ◽  
Hui Guo ◽  
Wei Peng ◽  
Qiao-Sheng Hu
Keyword(s):  
Room Temperature ◽  
Coupling Reactions ◽  
Aryl Chlorides
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