Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 4, 2024
Herein we successfully utilize various directing groups to achieve a ligand-enabled nickel-catalyzed 1,2-borylalkylation of unactivated alkenes. A β-amino alcohol was employed as the ligand for non-asymmetric alkenes, while bulky chiral diamine used asymmetric allyl amides.
Language: Английский
ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1693 - 1703
Published: Jan. 16, 2025
The enantioselective three-component dicarbonfunctionalization of electronically unactivated alkenes continues to pose a significant challenge. In this work, copper-catalyzed highly regio- and fluoroalkylalkynylation with diverse terminal alkynes fluoroalkyl halides under mild conditions is developed. addition halides, Togni's reagent can also participate in the reaction, delivering chiral β-trifluoromethyl high enantioselectivities. This method exhibits good functional group tolerance, facilitating late-stage derivatization variety biologically active molecules. success chemistry was achieved by using bulky indene-substituted BOPA ligand. DFT calculations indicate that radical through fluorine-directed outer-sphere pathway. Mechanistic studies reveal amide crucial for achieving stereoselectivities because exclusive F···H hydrogen bonding between Mes on be formed stabilize Si-radical coupling transition state.
Language: Английский
Citations
0
Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101261 - 101261
Published: Feb. 1, 2025
Language: Английский
Citations
0
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(20), P. 15790 - 15798
Published: Oct. 10, 2024
Here, we report a photoredox and nickel-catalyzed cross-electrophile coupling strategy for the asymmetric three-component 1,2-alkylarylation of vinyl boronates with (hetero)aryl bromides (2°, 3°)-alkyl redox-active esters in presence Hantzsch ester. With fluorinated pyridyl-substituted chiral biimidazoline ligand, this reaction enables straightforward access to wide variety synthetically valuable α-aryl from readily available starting materials. This features mild conditions, broad substrate generality, good functional group tolerance proceeds without using metal reductants or alkyl halides. Furthermore, alkenyl halides other electron-deficient alkenes such as acrylates phosphonates can be applied successfully. Preliminary mechanistic studies shed light on potential pathways roles organic amines.
Language: Английский
Citations
3
Published: Aug. 29, 2024
Here, an alcohol-directed 1,2-dicarbofunctionalization of alkenyl alcohols has been realized with aryl/alkenyl boronic acids and alkyl halides as the coupling partners. This reaction was enabled by a commercially available bulky 3-amyl β-diketone (Amacac) ligand, that enhancing reactivity suppressing many competitive processes. With alcohol weak native directing group, this protocol delivers 1,2-arylalkylated 1,2-alkenylalkylated high efficiency, regioselectivities, broad substrate scope, exceptional functional group tolerance. Notably, methodology facilitates modular synthesis biologically active compounds key alcohol-containing synthetic intermediates. Preliminary mechanistic studies shed light on neutral coordination functionality to nickel catalyst origin regioselectivity.
Language: Английский
Citations
1
Inorganic Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 3, 2024
Development of sustainable synthetic methods for the hydrosilylation alkenes, catalyzed by 3d transition metals, offers a promising alternative to traditional noble metal catalysts. This study presents computational mechanistic investigation into focusing on role ligands and centers in modulating reaction's mechanism regioselectivity. The ligand's electronic steric properties were found modulate regioselectivity cobalt catalysts, with phosphine ligand (xantphos) promoting higher linear selectivity compared nitrogen-based (
Language: Английский
Citations
1
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(24), P. 5061 - 5065
Published: Aug. 27, 2024
Abstract Herein, catalytic difunctionalization of vinyl arenes is reported using an iron salt as a catalyst without ligands. A series substituted alkylboronic acid esters was obtained single regioisomer from at 50 °C. This multicomponent protocol enabled the formation C−C and C−B bonds to produce boroalkylated products in process. non‐radical pathway proposed for reaction contrast radical pathways iron‐catalyzed hydroalkylation reactions. The organoboron compounds generated this were further utilized diverse functional group conversions.
Language: Английский
Citations
0
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(45), P. 30947 - 30957
Published: Oct. 30, 2024
New methods for the enantioselective synthesis of N-alkylated indoles and their derivatives are great interest because pivotal structural elements in biologically active molecules natural products. They also versatile intermediates organic synthesis. Among well-established asymmetric hydroamination methods, with indole-based substrates is a formidable challenge. This observation likely due to reduced nucleophilicity indole nitrogen. Herein, unique nickel-catalyzed enantio- branched-selective 2-azadienes structurally related N-heterocycles reported generation enantioenriched
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 4, 2024
Herein we successfully utilize various directing groups to achieve a ligand-enabled nickel-catalyzed 1,2-borylalkylation of unactivated alkenes. A β-amino alcohol was employed as the ligand for non-asymmetric alkenes, while bulky chiral diamine used asymmetric allyl amides.
Language: Английский
Citations
0