ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(33)
Published: Sept. 1, 2022
Abstract The complete series of chloro‐ and bromo‐cyclopentadienyl carbonyl complexes [(C 5 X n H 5‐n )Fe(CO) 2 R] (n=1–5, R=Me, Ph) could be prepared from the unsubstituted parent compounds via a sequence lithiations electrophilic halogenations. All four pentahaloyclopentadienyl were studied by X‐ray diffraction show an interplay weak intermolecular X…X, X…O X…H interactions.
Language: Английский
Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(9), P. 5297 - 5346
Published: Jan. 10, 2023
The combination of metal-, photo-, enzyme-, and/or organocatalysis provides multiple synthetic solutions, especially when the creation chiral centers is involved. Historically, enzymes and transition metal species have been exploited simultaneously through dynamic kinetic resolutions racemates. However, more recently, linear cascades appeared as elegant solutions for preparation valuable organic molecules combining bioprocesses metal-catalyzed transformations. Many advantages are derived from this symbiosis, although there still bottlenecks to be addressed including successful coexistence both catalyst types, need compatible reaction media mild conditions, or minimization cross-reactivities. Therefore, here also provided by means coimmobilization, compartmentalization strategies, flow chemistry, etc. A comprehensive review presented focusing on period 2015 early 2022, which has divided into two main sections that comprise first use metals independent catalysts but working in an orchestral sequential manner, later their application bionanohybrid materials coimmobilization adequate supports. Each part classified different subheadings, based catalyzed catalyst, while development nonasymmetric stereoselective processes was considered section.
Language: Английский
Citations
60
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(8), P. 5650 - 5660
Published: Feb. 15, 2024
We report a high throughput evaluation of the Mizoroki–Heck reaction diverse olefin coupling partners. Comparison different ligands revealed 1,5-diaza-3,7-diphosphacyclooctane (P2N2) scaffold to be more broadly applicable than common "gold standard" ligands, demonstrating that this family readily accessible diphosphines has unrecognized potential in organic synthesis. In particular, two structurally related P2N2 were identified enable regiodivergent arylation styrenes. By simply altering phosphorus substituent from phenyl tert-butyl group, both linear and branched products can obtained regioisomeric ratios. Experimental computational mechanistic studies performed further probe origin selectivity, which suggests coordinate metal similar manner but rigid positioning forces contact with incoming π–π interaction (for P-Ph ligands) or steric clash P-tBu ligands), dictating regiocontrol.
Language: Английский
Citations
7
Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(5), P. 1261 - 1287
Published: April 17, 2023
Language: Английский
Citations
14
Applied Catalysis A General, Journal Year: 2024, Volume and Issue: 676, P. 119638 - 119638
Published: Feb. 29, 2024
Language: Английский
Citations
3
Organic Letters, Journal Year: 2023, Volume and Issue: 25(33), P. 6217 - 6221
Published: Aug. 16, 2023
A highly diastereoselective Pd(0)-catalyzed Mizoroki-Heck reaction of gem-difluoroalkenes is described. Unlike previously reported C-F bond functionalization with organometallic reagents, this takes place between two different alkenes to achieve a formal and C-H cross-coupling via distinct pathway. Monofluorinated 1,3-diene products can be synthesized control the geometry each alkene good functional group tolerability.
Language: Английский
Citations
8
ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(15), P. 10085 - 10093
Published: July 18, 2023
A highly chemo- and regioselective decarboxylative Heck-type coupling of carboxylic acids terminal olefins has been developed using a catalytic system composed Pd(OAc)2 in the presence phosphine-sulfonamido ligands. Using bulky ligand L1 leads to high selectivity for 1,1-disubstituted (branched; b) that are generally difficult obtain. The influence all relevant reaction parameters was evaluated combination design experiments one factor at time optimization. dimethoxy-benzoic acid with various olefinic substrates gave corresponding branched excellent regioselectivity (b/l up 42:1) 80% isolated yields. In contrast, less L2 results inverse leading 1,2-disubstituted (linear; l) product again yield 86% = 1:26). Detailed investigation mechanistic pathways by DFT calculations reveals sterically demanding aryl substituent sulfonamide group favors pathway via 1,2-insertion an energy preference 4.4 kcal/mol, thus furnishing olefins. 2,1-insertion is advantageous 1.3 kcal/mol analogous linear products.
Language: Английский
Citations
4
Applied Organometallic Chemistry, Journal Year: 2022, Volume and Issue: 37(3)
Published: Dec. 19, 2022
Pd nanoparticle (Pd NP) immobilized on the magnetic Se and N dual‐doped carbon support was easily fabricated through thermal pyrolysis of glucose, selenium dioxide (SeO 2 ), ammonium chloride (NH 4 Cl), Fe 3 O hybridization followed by chemical reductive reaction. After successful characterization prepared Se‐mCN/Fe /Pd using various physicochemical techniques, it used as heterogeneous catalyst in Heck‐cross coupling The utilization cost‐effective biomass, high specific surface area, product conversion, generality diverse derivative simple separation process, four runs reusability are some benefits.
Language: Английский
Citations
7
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3562 - 3568
Published: Jan. 1, 2024
A method for the Mizoroki–Heck reaction of electron-deficient olefins acrylates with aryl bromides to obtain α-arylation products via a dual light/nickel catalytic system is described. This transformation features broad substrate scope, good functional group tolerance.
Language: Английский
Citations
1
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(23)
Published: April 10, 2023
The asymmetric total syntheses of (+)-vulgarisins A-E, which share a rare and highly oxygenated [5-6-4-5] tetracyclic core structure that were isolated from P. vulgaris Linn., have been described for the first time in divergent manner. Key transformations include: 1) catalytic intramolecular cyclopropanation to forge A ring bearing desired stereochemistry at C14; 2) one-pot borylation/conjugate addition process creation C1-C11 bond; 3) Wolff contraction assemble bicyclo[3.2.0]heptane subunit (CD rings); 4) stereocontrolled pinacol cyclization construction central B natural products.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8203 - 8226
Published: June 15, 2023
A Ni-catalyzed enantioselective intramolecular Mizoroki-Heck reaction has been developed to transform symmetrical 1,4-cyclohexadienes with attached aryl halides into phenanthridinone analogues containing quaternary stereocenters. Herein, we report important advances in optimization enabling control of unwanted proto-dehalogenation and alkene reduction side products. Moreover, this approach provides direct access six-membered ring heterocyclic systems bearing all-carbon stereocenters, which have much more challenging form enantioselectively nickel-catalyzed Heck reactions. wide range substrates were demonstrated work good excellent yields. Good enantioselectivity was using a new synthesized chiral iQuinox-type bidentate ligand (L27). The sustainability, low price nickel catalysts, significantly faster rate (1 h) versus that recently reported palladium-catalyzed (20 make process an attractive alternative.
Language: Английский
Citations
2