- Copper- and phosphane-free sonogashira coupling of arenediazonium o-benzenedisulfonimides
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Arenediazonium o-benzenedisulfonimides can be used as efficient reagents in Sonogashira coupling reactions. In this work, reactions were carried out in DMSO under very mild conditions (without copper or phosphanes), and gave rise to arylated alkynes in good to excellent yields (25 examples, average yield 83 %). o-Benzenedisulfonimide could be recovered from all the reactions in yields of >80 %, so it could be recycled for the preparation of other diazonium salts. Mechanistic insights revealed the fundamental roles of DMSO and the anion of o-benzenedisulfonimide in the formation of the catalyst, and also the importance of DMSO in the catalytic cycle. The Sonogashira coupling between are diazonium o-benzenedisulfonimides and terminal alkynes is a powerful method for the formation of arylated alkynes. No copper, phosphanes, bases, or co-catalysts are needed. Mechanistic insights highlighted the fundamental roles of DMSO and o-benzenedisulfonimide in the formation of the catalyst, and also the important role of DMSO in the catalytic cycle. Copyright
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
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- Iodolactonization of 3-Alkynylthiophene-2-Carboxylic and 3-Alkynylpicolinic Acids for the Synthesis of Fused Heterocycles
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The iodolactonization of 3-alkynylthiophene-2-carboxylic acids and 3-alkynylpicolinic acids has been investigated. Using I2 as the iodine source and NaHCO3 as the base in MeCN, the process took place smoothly to afford thienopyranone
- Gabriele, Bartolo,Mancuso, Raffaella,Novello, Mariangela,Palumbo Piccionello, Antonio,Russo, Patrizio
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supporting information
(2020/06/17)
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- Microwave-Assisted Synthesis of Sulfurated Heterocycles with Herbicidal Activity: Reaction of 2-Alkynylbenzoic Acids with Lawesson's Reagent
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The reactivity of 2-alkynylbenzoic acids toward Lawesson's reagent (LR) under microwave irradiation (300 W, 100 °C, CH2Cl2) was assessed. It was found that, depending on reaction conditions, either a dithionation- or a monothionation-cycloisomerization process takes place with formation of important sulfurated heterocycles. In particular, using 1 equivalent of LR for 1 h, dithionation occurred, with formation of benzo[c]thiophene-1(3H)-thiones or 1H-isothiochromene-1-thiones, while with 0.5 equiv. of LR for 10–30 min, monothionated products were selectively obtained (benzo[c]thiophen-1(3H)-ones or 1H-isothiochromen-1-ones). The regiochemical output of the process strongly depended on the substitution pattern of the starting 2-alkynylbenzoic acid derivatives. These compounds were also assayed as potential herbicides by assessing their phytotoxic activity on seedling growth and development of the model species Arabidopsis thaliana. All compounds, to different extents, influenced the morpho-physiological parameters that were monitored; in particular, the fresh weight (FW) was significantly affected, with ED50 values ranging from 4.81–63.7 μM.
- Giofrè, Salvatore V.,Mancuso, Raffaella,Araniti, Fabrizio,Romeo, Roberto,Iannazzo, Daniela,Abenavoli, Maria Rosa,Gabriele, Bartolo
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p. 942 - 950
(2019/07/31)
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- Green preparation method of 3-hydroxy isoindole-1-one compounds
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The invention discloses a green preparation method of 3-hydroxy isoindole-1-one compounds, and belongs to the technical field of organic synthesis. The method comprises the following steps: adopting 2-alkynyl benzamide as a reaction substrate, adding a br
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Paragraph 0039
(2020/01/03)
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- Copper- and Phosphane-Free Sonogashira Coupling of Arenediazonium o-Benzenedisulfonimides
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Arenediazonium o-benzenedisulfonimides can be used as efficient reagents in Sonogashira coupling reactions. In this work, reactions were carried out in DMSO under very mild conditions (without copper or phosphanes), and gave rise to arylated alkynes in good to excellent yields (25 examples, average yield 83 %). o-Benzenedisulfonimide could be recovered from all the reactions in yields of >80 %, so it could be recycled for the preparation of other diazonium salts. Mechanistic insights revealed the fundamental roles of DMSO and the anion of o-benzenedisulfonimide in the formation of the catalyst, and also the importance of DMSO in the catalytic cycle. The Sonogashira coupling between are diazonium o-benzenedisulfonimides and terminal alkynes is a powerful method for the formation of arylated alkynes. No copper, phosphanes, bases, or co-catalysts are needed. Mechanistic insights highlighted the fundamental roles of DMSO and o-benzenedisulfonimide in the formation of the catalyst, and also the important role of DMSO in the catalytic cycle.
- Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
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p. 598 - 605
(2015/10/05)
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- Palladacycle-catalyzed deacetonative sonogashira coupling of aryl propargyl alcohols with aryl chlorides
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An efficient and general protocol for the deacetonative Sonogashira coupling of aryl propargyl alcohols with aryl chlorides is described. The reaction proceeded smoothly with the catalyst system of palladacycle/Xphos. This result represents the first succ
- Hu, Hao,Yang, Fan,Wu, Yangjie
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p. 10506 - 10511
(2013/11/06)
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- Efficient synthesis of novel thieno[3,2-b]-, [2,3-c]- and [3,2-c]pyridones by Sonogashira coupling of bromothiophenes with terminal alkynes and subsequent intramolecular C-N bond-forming reaction
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The coupling of bromothiophenes with terminal alkynes using triethylamine or diisopropyl amine under Sonogashira conditions (PdCl2(PPh 3)2, CuI) followed by subsequent addition of amines or ammonium to the intermediate thienyl acetylenes represents a novel access to a wide range of thieno[3,2-b]-, [2,3-c]-, and [3,2-c]pyridones under basic conditions and in excellent yields.
- Iaroshenko, Viktor O.,Ali, Sajid,Babar, Tariq Mahmood,Abbasi, Muhammad S.A.,Sosnovskikh, Vyacheslav Ya,Villinger, Alexander,Tolmachev, Andrey,Langer, Peter
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p. 3167 - 3181
(2013/04/24)
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- A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH HETEROARYL TOSYLATES AND HETEROARYL BENZENESULFONATES
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The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), (I) wherein D, J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coup
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Page/Page column 31
(2009/03/07)
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