Stereoselective Synthesis of Vinyl Sulfones by the Stille Coupling of (E)-α-Stannylvinyl Sulfones with Aryl Halides

2008 ◽  
Vol 2008 (10) ◽  
pp. 592-594 ◽  
Author(s):  
Ronghua Hu ◽  
Yan Yu ◽  
Mingzhong Cai
Keyword(s):  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Stille Coupling ◽  
Co Catalyst ◽  
Stille Coupling Reaction ◽  
High Yields ◽  
Acetylenic Sulfones

Palladium-catalysed hydrostannylation of acetylenic sulfones (R–C≡C–SO2Ar) in benzene at room temperature gives stereoselectively (E)-α-stannylvinyl sulfones in good to high yields. (E)-α-Stannylvinyl sulfones are difunctional group reagents which undergo Stille coupling reaction with aryl halides in the presence of Pd(PPh3)4 and CuI co-catalyst to afford stereoselectively (Z)-1,2-disubstituted vinyl sulfones in good yields.

Synthesis of terminal arylacetylenes by a Stille coupling reaction catalysed by a MCM-41-supported bidentate phosphine palladium(O) complex

2008 ◽  
Vol 2008 (11) ◽  
pp. 615-618 ◽  
Author(s):  
Wenyan Hao ◽  
Yue Wang ◽  
Shouri Sheng ◽  
Mingzhong Cai
Keyword(s):  
Aqueous Medium ◽  
Palladium Catalyst ◽  
Basic Problem ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Stille Coupling ◽  
Bidentate Phosphine ◽  
Stille Coupling Reaction ◽  
High Yields ◽  
Mcm 41

A variety of terminal arylacetylenes have been conveniently synthesised in good to high yields by Stille coupling of aryl halides with ethynyltributylstannane catalysed by a MCM-41-supported bidentate phosphine palladium(O) complex in an aqueous medium and under air. Our system not only avoids the requirement for water-free and oxygen-free conditions, but also solves the basic problem of palladium catalyst reuse.

Regioselective fabrications of a Möbius aromatic [28]hexaphyrin palladium(II) complex

2013 ◽  
Vol 17 (08n09) ◽  
pp. 665-672 ◽  
Author(s):  
Tomoki Yoneda ◽  
Naoki Aratani ◽  
Atsuhiro Osuka
Keyword(s):  
Coupling Reaction ◽  
Molecular Topology ◽  
Stille Coupling ◽  
Topology Change ◽  
Bromide Ions ◽  
Stille Coupling Reaction ◽  
High Yields

Regioselective nucleophilic chlorination and bromination of [26]hexaphyrin to produce a [28]Möbius aromatic hexaphyrin Pd ( II ) complex were accomplished upon treatment of [26]hexaphyrin 2 with chloride and bromide ions in the presence of an acid with concurrent molecular topology change from Hückel to Möbius. Stille coupling reaction of the resultant 3-brominated complex 4 with ethynylstannanes afforded β-ethynylated derivatives in moderate to high yields.

An Easy Stereoselective Copper(I)-Catalyzed Synthesis of (E)-3-Trifluoromethylbut-2-en-3-ynoate via Palladium-Free Stille Coupling Reaction

Synlett ◽  
2012 ◽  
Vol 23 (05) ◽  
pp. 755-759 ◽  
Author(s):  
Mohamed Abarbri ◽  
Khalid Zine ◽  
Julien Petrignet ◽  
Jérôme Thibonnet
Keyword(s):  
Coupling Reaction ◽  
Stille Coupling ◽  
Stille Coupling Reaction

scholarly journals Synthesis of diaryl sulfides based on copper-doped OMS-2

2020 ◽  
pp. 174751982096698
Author(s):  
Shao-Qiang Yu ◽  
Na Liu ◽  
Ming-Guo Liu ◽  
Long Wang
Keyword(s):  
Manganese Oxide ◽  
Molecular Sieves ◽  
Copper Ions ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Environmental Friendliness ◽  
Good Tolerance ◽  
Catalytic Material ◽  
High Yields ◽  
Diaryl Sulfide

We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material can be recycled several times.

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