Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(21), P. 6114 - 6128
Published: Jan. 1, 2022
Hydrazines are versatile building blocks in organic synthesis.
Language: Английский
Precision Chemistry, Journal Year: 2023, Volume and Issue: 1(2), P. 112 - 118
Published: Feb. 10, 2023
Alkyl chlorides are robust precursors to carbon radicals; however, their relative inertness has hampered practical use. Although modern photochemical strategies have greatly enhanced the utility of alkyl as radical precursors, these methods often depend on strongly reducing conditions leading unproductive side reactions. Here, we report a catalytic generation from 1°, 2°, and 3° unactivated with zirconocene photoredox catalysis, which enables both hydrogenation borylation range structurally complex molecules. This mild zirconocene-catalyzed protocol shows that zirconium can render C–Cl bond cleavage more exergonic lower activation energy transition state, amplifying ability metallocenes toward halogen atom transfer.
Language: Английский
Citations
16
European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(12)
Published: Feb. 13, 2023
Abstract Organoboron compounds are versatile synthons in synthetic chemistry, materials science, and medicinal chemistry. The preparation of them often requires either reactive organometallic reagents or transition metals. In recent years, transition‐metal‐free borylation methodologies using radical chemistry for C−B bond formation have attracted much attention developed rapidly, which circumvents the use preformed reagents. Various successful approaches from different precursors (such as carboxylic acids, amines alcohols, abundant nature) through thermochemical, photochemical electrochemical pathways been developed. Therefore, this review, we hope to provide an overview advances discovery, development, mechanistic study processes.
Language: Английский
Citations
16
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(11), P. 2272 - 2294
Published: Jan. 1, 2023
This review presents a collective discussion on recent accomplishments in carbosilylation of alkenes and alkynes up to January 2023.
Language: Английский
Citations
15
Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 9020 - 9024
Published: Dec. 8, 2023
This study presents a novel method for the regioselective coupling of gem-difluorinated cyclopropanes with gem-diborylmethane, utilizing Pd-catalyst system. innovative approach enables synthesis 2-fluoroalkenyl monoboronate scaffolds high Z-selectivity. The resulting products undergo further transformations, including oxidation, Suzuki cross-coupling, and trifluoroborylation, all which are achieved good yields. work introduces valuable synthetic pathway to access important fluorinated compounds various applications in organic chemistry.
Language: Английский
Citations
14
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(11), P. 7210 - 7215
Published: March 4, 2024
Transition metal-catalyzed reductive cross-couplings to build C–C/Si bonds have been developed, but the cross-coupling create C(sp2)–B bond has not explored. Herein, we describe a nickel-catalyzed between aryl halides and bromoboranes construct bond. This protocol offers convenient approach for synthesis of wide range boronate esters, using readily available starting materials. Mechanistic studies indicate that key success reaction is activation B–Br with Lewis base such as 2-MeO-py. The ensures will react active nickel(I) catalyst prior halides, which different from sequence general C(sp2)–C/Si cross-coupling, where oxidative addition an halide proceeds first. Notably, this minimizes production undesired homocoupling byproduct without requirement excessive quantities either substrate.
Language: Английский
Citations
5
Chemical Science, Journal Year: 2023, Volume and Issue: 14(23), P. 6341 - 6347
Published: Jan. 1, 2023
The selective difunctionalization of N-heterocyclic carbene (NHC) boranes with alkenes has been achieved via decatungstate and thiol synergistic catalysis. catalytic system also allows stepwise trifunctionalization, leading to complex NHC three different functional groups which are challenging prepare by other methods. strong hydrogen-abstracting ability the excited enables generation boryl radicals from mono- di-substituted for realizing borane multifunctionalization. This proof-of-principle research provides a new chance fabricating unsymmetrical developing boron-atom-economic synthesis.
Language: Английский
Citations
12
Molecules, Journal Year: 2023, Volume and Issue: 28(2), P. 787 - 787
Published: Jan. 12, 2023
In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward establishment a resource-recycling society. organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and recycling elemental resources in mind, rather than just only synthesis. Many studies on construction frameworks functional molecules using ionic reactions transition-metal-catalyzed have reported, but most them focused formation carbon–carbon bonds. However, essential introduce appropriate groups at positions order for express their functions, furthermore, highly selective preparation multiple considered creation molecules. this review, we focus radical high group selectivity overview progress practical methods simultaneous introduction propose future that emphasize environmental friendliness.
Language: Английский
Citations
11
The Chemical Record, Journal Year: 2023, Volume and Issue: 23(11)
Published: June 12, 2023
Abstract Harnessing visible‐light in organic synthesis is one of the most effective methods that aligns with green and sustainable chemistry principles hence skyrocketed last two decades. Similarly, three‐component 1,2‐dicarbofunctionalization alkenes alkynes has recently been a great choice to construct complex molecular systems an easy rapid manner. Therefore, light‐induced reactions can be excellent alternative carry out reactions, very recently, chemists across globe have fascinated us their interesting articles. In this present review, we summarized recent advancements area visible light induced till March 2023. We categorized discussion based on catalysts used transformations for better understanding different important aspects these also covered.
Language: Английский
Citations
11
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: April 24, 2025
A novel electrochemical approach for the synthesis of hindered alkyl fluorides has been developed. The protocol grants access to a diverse array tertiary and secondary using readily attainable organoboron precursors under mild conditions. efficiency system stems from dual activation redox-active borate intermediate, providing both electrophilic nucleophilic reaction partners in form an internally generated ion pair.
Language: Английский
Citations
0
European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(45), P. 6115 - 6160
Published: Oct. 22, 2021
Abstract Organoboron compounds, especially alkenylboronates and arylboronates are highly useful reagents versatile building blocks in the modern synthetic chemistry toolbox. This review focuses on copper‐catalyzed routes to access alkenyl‐ arylboronate esters. Various copper salts ligands have been employed them excellent regio‐ stereoselectivity as well high yields. Both addition substitution reactions highlighted based various methodologies including hydroboration, carboboration, borylative opening of propargyl three‐ four‐membered rings, dehalogenative borylation alkenyl bromides iodides, defluoroborylation fluoroalkenes direct C(sp 2 )−H bond activation alkenes. Preparation involving aryl halides, arenes cascade 1,3‐halogen migration/borylation 2‐halostyrenes reviewed. Mechanistic aspects those discussed briefly.
Language: Английский
Citations
26