Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes

• Yajing Zhang,
• Qingshan Tian,
• Guozhu Zhang and
• Dayong Zhang

Beilstein J. Org. Chem. 2020, 16, 3086–3092, doi:10.3762/bjoc.16.258

• subsequent fluorine atom transfer. Keywords: β-fluorovinylphosphonates; fluorine atom transfer; P-centered radical; silver catalysis; three-component reaction; Introduction As one of the most important topics in organic chemistry, the introduction of fluorine and phosphorus atoms into double bonds is an

AgNTf₂-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives

• Ziping Cao,
• Jiekun Zhu,
• Li Liu,
• Yuanling Pang,
• Laijin Tian,
• Xuejun Sun and
• Xin Meng

Beilstein J. Org. Chem. 2019, 15, 2623–2630, doi:10.3762/bjoc.15.255

• use of an inexpensive catalyst, simple reaction conditions, simple work-up without column chromatographic purification for most of products and high yields. Keywords: [3 + 2] cycloaddition; isoxazole; pyrrole; silver catalysis; ynamide; Introduction Silver-catalyzed transformations of alkynes have

• -mediated reactions of alkynes (Scheme 1, path b). In 2007, Echavarren and co-workers have developed an intramolecular cyclopropanation reaction of 1,6-enynes by silver catalysis, involving probably the generation of a silver-carbene species [15]. Wang and co-workers reported a range of propargylic esters

• carbene pathway presumed by mechanistic studies and theoretical calculations. Following our ongoing interest in the alkyne chemistry [36][37][38], we recently envisaged that the reaction of ynamides with isoxazoles could proceed under silver catalysis conditions, involving the generation of α-imino silver

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• -diphenylanthracene [56][57]. The silver(I) coordination on the ligand and the formation of supramolecular systems does not seem to affect the spectroscopic properties of the 9,10-diphenylanthracene system. Silver catalysis As silver(I) salts exhibit a high alkynophilicity [11][12][13][14][15][16][17], the new

• ; homogeneous catalysis; prochiral; silver complex; thioether ligand; Introduction Since the early advances in the late eighties [1][2][3][4][5][6][7][8][9][10], silver(I) catalysis has been widely exploited based on the versatile redox and soft Lewis acid properties of this coinage metal cation. Silver

• catalysis has proved its effectiveness for numerous transformations involving unsaturated bond activation (allene, alkyne, alkene) [11][12][13][14][15][16][17], radical-based reactions [18][19][20] and several applications in asymmetric reactions [21][22]. This successful chemistry was usually conducted in

Silver and gold-catalyzed multicomponent reactions

• Giorgio Abbiati and
• Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

• -coupling products into tandem reactions. The second goal could be achieved by classifying reactions on the basis of the involved reactants, the reaction type or the role of the catalyst. Review A3-coupling-type reactions Silver catalysis The catalytic direct 1,2-addition of alkynes to imines and iminium

• dealing with the use of BINAP–AgClO4 as a chiral catalyst in the same two-component reaction [98]. Higher enantioselectivities were rarely observed with SbF6− being the weaker coordinating counter ion. An interesting application of silver catalysis in the allene chemistry field has been recently proposed

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

• Sebastian Krüger and
• Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

• to give pentacycle 172. Reduction of the nitro group was followed by Cbz-protection. Allylic alcohol 173 resulted from radical allylic bromination followed by displacement of bromine through water under silver-catalysis. Eschenmoser–Claisen rearrangement [148] led to the formation of the remaining

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

• Kei Murakami and
• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34

•  37). Although the cobalt-catalyzed allylzincation reactions of dialkylacetylenes resulted in low yield, the reactions of arylacetylenes provided various tri- or tetrasubstituted styrene derivatives (Scheme 38) [119][120]. Kambe reported a rare example of silver catalysis for carbomagnesiation