Mechanochemical Synthesis of Diarylethynes from Aryl Iodides and CaC2

Synlett ◽  
2022 ◽  
Author(s):  
Pit van Bonn ◽  
Carsten Bolm
Keyword(s):  
Mechanochemical Synthesis ◽  
Palladium Catalyst ◽  
Calcium Carbide ◽  
Copper Salt ◽  
Aryl Iodides

A mechanochemical synthesis of diarylethynes from aryl iodides and calcium carbide as acetylene source is reported. The reaction is catalyzed by a palladium catalyst in the presence of copper salt, base and ethanol as liquid assisting grinding (LAG) additive. Various aryl and heteroaryl iodides have been converted in up to excellent yields.

Ambient-Temperature Ortho C–H Arylation of Benzoic Acids with Aryl Iodides with Ligand-Supported Palladium Catalyst

2015 ◽  
Vol 17 (14) ◽  
pp. 3418-3421 ◽  
Author(s):  
Changlei Zhu ◽  
Yuanfei Zhang ◽  
Jian Kan ◽  
Huaiqing Zhao ◽  
Weiping Su
Keyword(s):  
Ambient Temperature ◽  
Palladium Catalyst ◽  
Benzoic Acids ◽  
Supported Palladium Catalyst ◽  
Aryl Iodides ◽  
Supported Palladium

Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 581-590 ◽  
Author(s):  
Zhaotao Xu ◽  
Bin Huang ◽  
Zebiao Zhou ◽  
Mingzhong Cai
Keyword(s):  
Carbon Monoxide ◽  
Palladium Catalyst ◽  
Functional Group ◽  
Atom Economy ◽  
Highly Efficient ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
High Yields

A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N,N-diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.

scholarly journals Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide

2013 ◽  
Vol 9 ◽  
pp. 2404-2409 ◽  
Author(s):  
Yuzo Nakamura ◽  
Motohiro Fujiu ◽  
Tatsuya Murase ◽  
Yoshimitsu Itoh ◽  
Hiroki Serizawa ◽  
...  
Keyword(s):  
Copper Salt ◽  
Catalytic Reactions ◽  
Metal Fluoride ◽  
Reaction Conditions ◽  
Aryl Iodides ◽  
Silyl Groups ◽  
High Yields

The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated products in moderate to high yields. The advantage of this method is that additives such as metal fluoride (MF), which are indispensable to activate silyl groups for transmetallation in the corresponding reactions catalyzed by copper salt by using the Ruppert–Prakash reagents (CF3SiR3), are not required.

Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

2020 ◽  
Vol 7 (19) ◽  
pp. 2938-2943
Author(s):  
Yeojin Kim ◽  
Kwang Ho Song ◽  
Sunwoo Lee
Keyword(s):  
Aryl Iodide ◽  
Aryl Iodides ◽  
Palladium Catalyzed

Aryl sulfonyl hydrazide reacted with aryl iodide in the presence of CO to give the corresponding S-aryl thioesters.

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