Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review

• Daniel S. Müller

Beilstein J. Org. Chem. 2026, 22, 1–63, doi:10.3762/bjoc.22.1

• is generated in situ and likely present only in trace amounts. All our attempts to accelerate the reaction through addition of various mono- and bidentate phosphorus ligands were unsuccessful. A similar trend was observed with NEt3, which afforded optimal yields at 20–30 mol % loading (not shown

Synthesis of medium and large phostams, phostones, and phostines

• Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

• –elimination. Both they are potential chiral phosphorus ligands (Scheme 20) [25]. When Fuchs and co-workers investigated the conversion of cyclic vinyl sulfones to vinylphosphonates, they found that the reaction of (1S,2R)-2-methyl-3-(phenylsulfonyl)cyclohept-3-en-1-ol (100) and diethyl phosphonate generated

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes

• Almaz A. Zagidullin,
• Farida F. Akhmatkhanova,
• Mikhail N. Khrizanforov,
• Robert R. Fayzullin,
• Tatiana P. Gerasimova,
• Ilya A. Bezkishko and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139

• objects of growing interest in the fields of coordination chemistry [3][4][5] and asymmetric catalysis [6][7]. Due to the sp2-hybridization of the phosphorus atom, phosphaferrocenes are commonly regarded as phosphorus ligands with weaker σ-donor character than classical tertiary phosphines and stronger π

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• the glycolytic depolymerisation of PET [128][205]. The highest BHET yield (74.7%) was achieved using zinc chloride (0.5% w/w), an EG/PET ratio of 14:1 and reflux conditions (Table 2, entry 8). The use of preformed soluble Co(II) complexes bearing bidentate phosphorus ligands (e.g., 1,2-bis

Pd(OAc)₂/Ph₃P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles

• Dominik Kellner,
• Maximilian Weger,
• Andrea Gini and
• Olga García Mancheño

Beilstein J. Org. Chem. 2017, 13, 1807–1815, doi:10.3762/bjoc.13.175

• Beller and co-workers (Scheme 1, reaction 2) [33]. The use of NHCs proved to be the key, since the more accessible monodentated phosphorus ligands such as triphenyl (Ph3P) or tricyclohexyl (Cy3P) phosphines showed a significant lower efficiency and different selectivity with the same palladium source Pd

P(O)R₂-directed Pd-catalyzed C–H functionalization of biaryl derivatives to synthesize chiral phosphorous ligands

• Rong-Bin Hu,
• Hong-Li Wang,
• Hong-Yu Zhang,
• Heng Zhang,
• Yan-Na Ma and
• Shang-dong Yang

Beilstein J. Org. Chem. 2014, 10, 2071–2076, doi:10.3762/bjoc.10.215

• . China 10.3762/bjoc.10.215 Abstract Chiral phosphorus ligands have been widely used in transition metal-catalyzed asymmetric reactions. Herein, we report a new synthesis approach of chiral biaryls containing a phosphorus moiety using P(O)R2-directed Pd-catalyzed C–H activation; the functionalized

• products are produced with good enantioselectivity. Keywords: chiral synthesis; Pd-catalysis; organophosphorus; phosphorus ligands; P(O)R2-directing; Introduction In the past decades, phosphorus ligands have been demonstrated to be efficient ligands in many metal-catalyzed organic reactions [1][2][3][4

• group not only achieved the directing role but also acts as an important component unit of the C–H functionalized products. In this paper, we use the axially chiral biaryl phosphine oxides as substrates and report the synthesis of various chiral phosphorus ligands with high enantiomeric selectivity

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• CuAAC catalysis. With this ligand (30 mol %) and copper(I) bromide (5 mol %) the reaction of benzyl azide with phenylacetylene is completed within 10 minutes in aqueous solution at room temperature under aerobic conditions [118]. Phosphorus ligands in combination with copper(I) salts have been reported

• ). As copper(I) thiolate complexes show a high tendency to form aggregates [133][134][135][136], speciation and nuclearity of the catalytically active species remain unknown. Copper(I) complexes with phosphorus ligands, for example the commercially available air-stable salts [CuBr(PPh3)3] and {CuI[P(OEt

Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

• trifluoromethylated arenes in good yields, and a variety of functional groups is tolerated under the mild conditions of the process. The reaction with aryl bromides or triflates is less efficient. The success of this Pd-catalyzed trifluoromethylation is due to highly hindered phosphorus ligands like BrettPhos, which

Air-stable, recyclable, and time-efficient diphenylphosphinite cellulose-supported palladium nanoparticles as a catalyst for Suzuki–Miyaura reactions

• Qingwei Du and
• Yiqun Li

Beilstein J. Org. Chem. 2011, 7, 378–385, doi:10.3762/bjoc.7.48

• synthesis of ligands [5][6]. In the past few years, many efficient and selective catalytic systems have been developed for the reaction. A considerable number of homogenous palladium catalysts have been used to obtain high yields of a desired product [7][8][9], for example, phosphorus ligands [10][11][12

A superior P-H phosphonite: Asymmetric allylic substitutions with fenchol- based palladium catalysts

• Bernd Goldfuss,
• Thomas Löschmann,
• Tina Kop-Weiershausen,
• Jörg Neudörfl and
• Frank Rominger

Beilstein J. Org. Chem. 2006, 2, No. 7, doi:10.1186/1860-5397-2-7

• the challenging 1-phenyl-2-propenyl acetate (Scheme 1, R=Ph) [27][28]. Results and discussion Fenchylphosphinites (FENOPs) and biphenylbisfenchol based phosphorus ligands are all suitable for Pd-catalyzed allylic alkylations of 1-phenyl-2-propenyl acetate (Scheme 4, Table 1, see Supporting Information

• ). Bidentate P, N-ligands and a monodentate phosphoramidite for Pd-catalyzed allylic substitutions with unsymmetric substrates, cf. Scheme 1. Fenchole-based phosphorus ligands (i.e. FEENOPs and BIFOPs) for Pd-catalyzed allylic substitutions. Pd-π arene or Pd-N coordinations give rise to different

An exceptional P-H phosphonite: Biphenyl- 2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper- catalyzed 1,4-additions

• T. Kop-Weiershausen,
• J. Lex,
• J.-M. Neudörfl and
• B. Goldfuss

Beilstein J. Org. Chem. 2005, 1, No. 6, doi:10.1186/1860-5397-1-6

• as well as hydridic and organometallic nucleophiles. Chloride substitution in BIFOP-Cl proceeds only under drastic conditions. New enantiopure, sterically demanding phosphorus ligands such as a phosphoramidite, a phosphite and a P-H phosphonite (BIFOP-H) are hereby accessible. In enantioselective Cu

• -catalyzed 1,4-additions of ZnEt2 to 2-cyclohexen-1-one, this P-H phosphonite (yielding 65% ee) exceeds even the corresponding phosphite and phosphoramidite. Keywords: phosphorus ligands; chirality; biaryls; asymmetric conjugate additions; phosphoramidites; phosphites; phosphonites; X-ray analyses

• ; Introduction Chiral monodentate phosphorus ligands with C2-symmetric diol backbones, e.g. with the prominent BINOLs or TADDOLs, are fundamental for the construction of efficient enantioselective transition metal catalysts, especially for copper-catalyzed 1,4-additions. [1][2][3][4][5][6][7][8][9][10][11][12