Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• aryldiazonium ion, which is generated in situ from the corresponding arylamine. At the same time, a copper-catalyzed Sandmeyer trifluoromethylation of arenediazonium tetrafluoroborates was also reported by the group of Gooßen (Scheme 25) [44]. This reaction was conducted under mild conditions using TMSCF3 as

• (tpy) and a small amount of water as the co-solvent. A range of arenediazonium tetrafluoroborates were smoothly converted to the corresponding analogues in acceptable yields. A mechanistic study indicated that a radical process was involved in this conversion (Scheme 28). First, the diazo radical

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS₂

• Jing Leng,
• Shi-Meng Wang and
• Hua-Li Qin

Beilstein J. Org. Chem. 2017, 13, 903–909, doi:10.3762/bjoc.13.91

• visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields. Keywords: arenediazonium

• -mediated coupling of arenediazonium tetrafluoroborates and CS2 for the chemoselective assembly of diaryl disulfides as our continuing endeavor of utilizing arenediazonium tetrafluoroborates [16] for synthetic applications (Scheme 1). We conducted our initial study with benzenediazonium tetrafluoroborate

• arenediazonium tetrafluoroborates was utilized in the reaction with CS2 to generate the corresponding diaryl disulfides (Table 4). Arenediazonium tetrafluoroborates 1b–p with both, electron-withdrawing and donating groups successfully underwent transformation, affording the corresponding coupling products 3b–p

Matsuda–Heck reaction with arenediazonium tosylates in water

• Ksenia V. Kutonova,
• Marina E. Trusova,
• Andrey V. Stankevich,
• Pavel S. Postnikov and
• Victor D. Filimonov

Beilstein J. Org. Chem. 2015, 11, 358–362, doi:10.3762/bjoc.11.41

• ]. In 2012, examples of the Matsuda–Heck arylation of styrene and acrylic acid esters with arenediazonium tetrafluoroborates in water and catalyzed with in situ formed Pd nanoparticles [5] or agarose-supported Pd nanoparticles [6] have been reported. Superparamagnetic Pd–ZnFe2O4 MNPs have been shown to

• described by the group of Vallribera [9]. Arenediazonium tetrafluoroborates bearing only electron-donating groups (with the exception of chlorine) were effectively coupled with ethyl and tert-butyl acrylates only, while ethyl vinyl ketone, styrenes, allyl acetate, allyl benzene and methyl vinyl carbinol

• were rather less reactive under these conditions, and products were obtained with low to modest yields [9]. Previously, we described a novel type of diazonium salt – arenediazonium tosylates (ADT), which differ from arenediazonium tetrafluoroborates in their higher stability at a dry state and their

Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

• Silvia M. Soria-Castro and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2013, 9, 467–475, doi:10.3762/bjoc.9.50

• ] and sulfonamides [49]. Thioacetate and thiobenzoate derivatives have been synthesized by the reactions of thioacetate and thiobenzoate anions with arenediazonium tetrafluoroborates [50]. However, this methodology implies moderate overall yields and the handling of usually unstable diazonium salts